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

HRID 1767962ノート

反応式

HRID 1767962 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-934ba1ff04014c8ab7b6b184425d1190
出典データセット
uspto-grants-2007_06
特許番号
US07235572B2

反応ノート

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