Category: 59247-47-1

59247-47-1, These common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a 25 mL sealed tube was added 5-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-L2-oxazol-4-yl]methoxy ]-3-methyl-2-azabicydo[2.2.l]heptane trifluoroacetic acid salt 360m(250 mg, 0.49 mmol, 1.00 equiv.), tert-buty 4-bromobenzoate (196 mg, 0.76 mmol, 1.5010 equiv.), Ruphos precatalyst (lOS rng, 0.20 equiv ), Ruphos (59.5 mg, 0.20 equiv.), tol (6 mL),and Cs2CCh (595 mg, 1.83 mmol, 3.00 equiv.). The resulting mixture was heated at 110 ¡ãCovernight. After cooling to room temperature, f-hO (l 00 mL) was added, the mixture wasextracted ¡¤with ethyl acetate (lOO mL x 2). The combined organic extracts vvere washed withbrine (200 mL x 2), dried over anhydrous sodium sulfate, and concentrated under vacuum15 The residue was purified by silica gel column chromatography eluting with ethylacetate/petroleum ether (1:3) to give tert-butyl 4-(5-[[5-cydopropyl-3-(2,6-dichloropheny l)-1 ,2-oxazol-4-yl]methoxy]-3-methyl-2-azabicyclo[2.2.l ]hept:m-2-yl)benzoate 360n (230 mg,81 percent) as a light yellow foam

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 59247-47-1.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

59247-47-1, Adding some certain compound to certain chemical reactions, such as: 59247-47-1, name is tert-Butyl 4-bromobenzoate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 59247-47-1.

To a mixture of tert-butyl 4-bromobenzoate (10.07 g, 39.2 mmol), K3PO4 (20.19 g, 95 mmol), and dimethyl malonate (4.50 mL, 39.2 mmol) was added toluene (69 mL), Pd2(dba)3 (975 mg, 1.08 mmol), and .yen.(tert-Bu)3 (12.8 mL, 10percent wt. in hexanes, 4.3 mmol). The reaction mixture was degassed and heated to 85¡ãC. After 2 d, the reaction mixture was diluted with ethyl acetate, washed with water (1 x), brine (1 x), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (5percent to 20percent ethyl acetate in hexanes) gave dimethyl [4-(fe/t-butoxycarbonyl)phenyl]malonate as a low melting white solid: 1HNMR (600 MHz, CDCl3) delta 7.98 (d, J = 8.5 Hz, 2H), 7.45 (d, J = 8.2 Hz, 2H), 4.70 (s, IH), 3.76 (s, 6H), 1.58 (s, 9H); ESIMS calcd 331.1 (Mi + Na), found 331.1 (Mi + Na).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 59247-47-1.

Reference:
Patent; MERCK & CO., INC.; WO2007/55941; (2007); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

59247-47-1, Adding some certain compound to certain chemical reactions, such as: 59247-47-1, name is tert-Butyl 4-bromobenzoate, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 59247-47-1.

Example 30 Preparation of 4-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenoxy}-pyrrolidin-1-yl)-benzoic acid To a mixture of 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid [4-((S)-pyrrolidin-3-yloxy)-phenyl]-amide hydrochloride (180 mg, 0.37 mmol), 4-bromobenzoic acid tert-butyl ester (114 mg, 0.44 mmol), sodium tert-butoxide (118 mg, 1.23 mmol) and (2′,4′,6′-triisopropyl-1,1′-biphenyl-2-yl)dicyclohexylphosphine (X-PHOS, 40 mg) in dioxane (5 mL) bubbled with argon was added tris(dibenzylideneacetone)dipalladium Pd2(dba)3 (24 mg). The mixture was heated at 105¡ã C. for 2 hrs. Solvents were evaporated and the residue was extracted with ethyl acetate and 0.1N hydrochloric acid. The organic layer was dried and concentrated. The residue was purified through ISCO column chromatography (silica gel, ethyl acetate in hexane, 5percent to 60percent linear gradient) to give a white solid as 4-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenoxy}-pyrrolidin-1-yl)-benzoic acid tert-butyl ester (150 mg, yield 69percent). The above 4-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenoxy}-pyrrolidin-1-yl)-benzoic acid tert-butyl ester (150 mg) was dissolved in a mixture of methylene chloride (2 mL) and trifluoroacetic acid (4 mL). The mixture was stirred at room temperature for 1 hr and solvents were evaporated. The residue was extracted with ethyl acetate and water. The organic layer was dried and solvents were evaporated. The residue was triturated with ethyl acetate and hexanes to give a tan solid as 4-((S)-3-{4-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-phenoxy}-pyrrolidin-1-yl)-benzoic acid (75 mg). LC-MS for C28H22F3N3O5 (m/e) calcd 537, obsd 538 (M+H).

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 59247-47-1.

Reference:
Patent; Bolin, David Robert; Cheung, Adrian Wai-Hing; Firooznia, Fariborz; Marcopulos, Nicholas; Qian, Yimin; US2010/152445; (2010); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

59247-47-1, These common heterocyclic compound, 59247-47-1, name is tert-Butyl 4-bromobenzoate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a 50-mL round-bottom flask was added (1 S,4S,.5R)-.5-[[5-cyclopropyl-3-(2,6-dichlorophenyl)- L2-oxazol-4-yl]methoxy]-2-azabicyclo[2.2.1 ]heptane 12d (800 mg, 2.11mmol, 1.0 equiv.), tert-buty 4-bromobenzoate 52b (650 mg, 2.53 mmol, 1.20 equiv.),Pd2(dba)3 (190 mg, 0.21 mmol, 0.10 equiv.), BINAP (130 mg, 0.21 mmol, 0.10 equiv),Cs2C01 (960 mg, 2.9.5 mmoL 1.40 equiv.), and toluene (.5 mL) and the resulting mixture was20 stirred at 110 ¡ãC overnight. After cooling to room temperature, l 00 mL of I-hO v.¡¤as addedand the aqueous mixture was extracted with ethyl acetate (l 00 mL x 2). Tiw combinedorganic extracts were washed with brine (100 mL x 2), dried over anbydrous sodium sulfate,filtered, and concentrated under reduced pressure. The residue was purified by silica gelcolumn chromatography eluting vvith ethyl acetate/petroleum ether (1 :6) to give 0.55 g (4Tpercent)25 of tert-buiyl 4-[(1 S,4S,5R)-.5-[[5-cyclopropyl-3-(2,6-dichlorophenyl)-l ,2-oxazol-4-yl]methoxy ]-2-azabicyclo[2.2.1 ]heptan-2-yl]benzoate 52c as a light green solid.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 59247-47-1.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics