Potassium Carbonate → 5-[1-Biphenyl-4-ylmethyl-4,6-difluoro-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazol-2-yloxy]-2-methyl-benzoic acid methyl ester

HRID 1945296노트

반응식

HRID 1945296 반응식
[C:1]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([F:28])[C:15]([C:18]4[CH:19]=[C:20]5[C:24](=[CH:25][CH:26]=4)[N:23]([CH3:27])[CH:22]=[CH:21]5)=[C:16]([F:17])[C:11]=3[N:10]=[C:9]2S(C)(=O)=O)=[CH:3][CH:2]=1.[CH3:39][O:40][C:41](=[O:50])[C:42]1[CH:47]=[C:46]([OH:48])[CH:45]=[CH:44][C:43]=1[CH3:49].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:39][O:40][C:41](=[O:50])[C:42]1[CH:47]=[C:46]([O:48][C:9]2[N:8]([CH2:7][C:4]3[CH:5]=[CH:6][C:1]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:2][CH:3]=3)[C:12]3[CH:13]=[C:14]([F:28])[C:15]([C:18]4[CH:19]=[C:20]5[C:24](=[CH:25][CH:26]=4)[N:23]([CH3:27])[CH:22]=[CH:21]5)=[C:16]([F:17])[C:11]=3[N:10]=2)[CH:45]=[CH:44][C:43]=1[CH3:49]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 13929055Methyl 5-hydroxy-2-methylbenzoateHCID 686594621-biphenyl-4-ylmethyl-4,6-difluoro-2-methanesulfonyl-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazole

생성물 1

HCID 685739675-[1-Biphenyl-4-ylmethyl-4,6-difluoro-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazol-2-yloxy]-2-methyl-benzoic acid methyl ester

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
130 °C

실험 절차

A solution of 1-biphenyl-4-ylmethyl-4,6-difluoro-2-methanesulfonyl-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazole (1088 mg, 2.1 mmol), 5-hydroxy-2-methyl-benzoic acid methyl ester (513 mg, 3.1 mmol) and potassium carbonate (580 mg, 4.2 mmol) in DMF (20 mL) was stirred at room temperature under nitrogen. After 18 h, the reaction mixture was transferred to a microwave vial and heated under microwave at 130° C. for 10 min. The cooled reaction mixture was diluted with EtOAc and washed 3 times with saturated ammonium chloride, dried (MgSO4), filtered, and concentrated. Chromatography over silica gel afforded the desired product as a colorless foam.

후처리

  1. customThe cooled reaction mixture
  2. washwashed 3 times with saturated ammonium chloride
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-4a3e6e204c524f6db78196791ca3cb7e
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08394969B2

반응 노트

불러오는 중…