Diethyl Ether → 5-({4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methoxy)-1H-indole

HRID 1767962노트

반응식

HRID 1767962 반응식
C([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[NH:5][CH:4]=1)C.Cl[CH2:14][C:15]1[S:19][C:18]([C:20]2[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=2)=[N:17][C:16]=1[CH3:30].C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)C>CN(C=O)C>[CH3:30][C:16]1[N:17]=[C:18]([C:20]2[CH:21]=[CH:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=2)[S:19][C:15]=1[CH2:14][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][CH:4]=[CH:3]2

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 27830065-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazoleHCID 153663373-ethyl-1H-indol-5-ol

생성물 1

HCID 219494915-({4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methoxy)-1H-indole수율 91.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A suspension of 3-ethyl-1H-indol-5-ol (235 mg, 1.46 mmol), 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole [425 mg, 1.46 mmol; PCT Int. Appl. (2002), WO 0292590 A1] and cesium carbonate (712 mg, 2.19 mmol) in DMF (3 ml) was stirred for 1.5 h at ambient temperature. Diethyl ether was added and the mixture was washed with 1N HCl and water. The organic layer was dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (silica gel, ethyl acetate/heptane 1:3) to give 522 mg (1.34 mmol, 86%) 5-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-1H-indole.

후처리

  1. washthe mixture was washed with 1N HCl and water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by column chromatography (silica gel, ethyl acetate/heptane 1:3)

출처 및 근거

ORD 기록
ord-934ba1ff04014c8ab7b6b184425d1190
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07235572B2

반응 노트

불러오는 중…