HRID1691951

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID516892

Sodium Bicarbonate

CHNaO3

HCID642811

3-Amino-6-bromopyridine

C5H5BrN2

HCID2776438

2-Phenyl-5-(trifluoromethyl)oxazole-4-carboxylic acid

C11H6F3NO3

结构：COC(=O)C1CCCC1C(=O)c1ccc(B2OC(C)(C)C(C)(C)O2)cc1

HCID21985874

未命名化合物

结构：O=C(Nc1ccc(Br)nc1)c1nc(-c2ccccc2)oc1C(F)(F)F

HCID57652145

未命名化合物

PRODUCTS

生成物

结构：COC(=O)C1CCCC1C(=O)c1ccc(-c2ccc(NC(=O)c3nc(-c4ccccc4)oc3C(F)(F)F)cn2)cc1

HCID25122186

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

结构：[Pd].c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1.c1ccc(P(c2ccccc2)c2ccccc2)cc1

催化剂HCID11979704

未命名化合物

溶剂HCID702

Ethanol

C2H6O

溶剂HCID1140

Toluene

C7H8

CONDITIONS

反应条件

温度: 160 °C

PROCEDURE

实验过程

2-(4-{5-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoyl)-cyclopentanecarboxylic acid methyl ester was prepared through a standard Suzuki coupling procedure by mixing 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid (6-bromo-pyridin-3-yl)-amide (prepared using a similar coupling procedure as described above from 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid and 6-bromo-pyridin-3-ylamine), 2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoyl]-cyclopentanecarboxylic acid methyl ester, palladium tetrakis(triphenylphosphine) and aqueous sodium bicarbonate solution in toluene and ethanol, and heating this mixture to 160° C. under microwave condition for 20 min. Aqueous workup followed by silica gel chromatography separation gave 2-(4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoyl)-cyclopentanecarboxylic acid methyl ester as light yellow solid. LCMS calcd for C30H24F3N3O5 (m/e) 563, obsd 564 (M+H).

WORKUP

后处理

custom2-(4-{5-[(2-Phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoyl)-cyclopentanecarboxylic acid methyl ester was prepared through a standard Suzuki coupling procedure
customprepared
customAqueous workup followed by silica gel chromatography separation

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-630040547ecb4903acf40a66f97305a6
来源数据集: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08153644B2
来源说明: uspto-grants-2012_04

反应 SMILES

Br[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[N:12]=[C:13]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[O:14][C:15]=2[C:16]([F:19])([F:18])[F:17])=[O:10])=[CH:4][CH:3]=1.C1(C2OC(C(F)(F)F)=C(C(O)=O)N=2)C=CC=CC=1.BrC1N=CC(N)=CC=1.[CH3:52][O:53][C:54]([CH:56]1[CH2:60][CH2:59][CH2:58][CH:57]1[C:61](=[O:77])[C:62]1[CH:67]=[CH:66][C:65](B2OC(C)(C)C(C)(C)O2)=[CH:64][CH:63]=1)=[O:55].C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C(O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:52][O:53][C:54]([CH:56]1[CH2:60][CH2:59][CH2:58][CH:57]1[C:61](=[O:77])[C:62]1[CH:63]=[CH:64][C:65]([C:2]2[CH:3]=[CH:4][C:5]([NH:8][C:9]([C:11]3[N:12]=[C:13]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[O:14][C:15]=3[C:16]([F:18])([F:19])[F:17])=[O:10])=[CH:6][N:7]=2)=[CH:66][CH:67]=1)=[O:55]