Cesium carbonate → Methyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

HRID 486093노트

반응식

HRID 486093 반응식
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[C:9]([S:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[C:8]2[CH2:22][C:23]([CH3:29])([CH3:28])[C:24]([O:26][CH3:27])=[O:25])=[CH:4][CH:3]=1.Cl.Cl[CH2:34][C:35]1[N:36]=[C:37]([CH3:40])[S:38][CH:39]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:34][C:35]4[N:36]=[C:37]([CH3:40])[S:38][CH:39]=4)=[CH:13][CH:14]=3)[C:9]([S:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[C:8]2[CH2:22][C:23]([CH3:29])([CH3:28])[C:24]([O:26][CH3:27])=[O:25])=[CH:30][CH:31]=1

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 27342034-(Chloromethyl)-2-methyl-1,3-thiazole--hydrogen chloride (1/1)HCID 14980577Methyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-hydroxy-1H-indol-2-yl)-2,2-dimethylpropanoate

생성물 1

HCID 19097505Methyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-(2-methylthiazol-4-ylmethoxy)indol-2-yl]-2,2-dimethylpropanoate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of methyl 3-[1-(4-chlorobenzyl)-3-(t-butylthio)-5-hydroxyindol-2-yl]-2,2-dimethylpropanoate (Preparation 2) (25 g), 4-chloromethyl-2-methylthiazole hydrochloride (Maybridge Chemical Co., Ltd.) (11.6 g) and Cs2CO3 (68.7 g) in 250 mL of CH3CN were heated at reflux for 24 hours. The mixture was cooled, poured onto water, and extracted (2× EtOAc), washed twice with brine, dried (MgSo4), and evaporated. Chromatography of the residue on silica gel eluting with hexane/EtOAc 4:1 afforded the title compound as a solid.

후처리

  1. temperatureat reflux for 24 hours
  2. temperatureThe mixture was cooled
  3. additionpoured onto water
  4. extractionextracted (2× EtOAc)
  5. washwashed twice with brine
  6. customdried (MgSo4)
  7. customevaporated

출처 및 근거

ORD 기록
ord-0f741723648b47b78d6eebd137cf3032
출처 데이터셋
uspto-grants-1994_03
특허 번호
US05290798

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