Potassium Carbonate → 1-Benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-6-(1,3-thiazol-2-yloxy)-1H-indole-3-carboxamide

HRID 40128

反応式

HRID 40128 の反応式
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[C:10]([C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=2)=[O:19])=[C:9]1[CH:30]([CH3:32])[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[C:40]1[S:41][CH:42]=[CH:43][N:44]=1.[OH-].[Na+]>CN(C=O)C.CCOC(C)=O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][C:40]3[S:41][CH:42]=[CH:43][N:44]=3)[CH:15]=2)[C:10]([C:18]([NH:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=2)=[O:19])=[C:9]1[CH:30]([CH3:32])[CH3:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 764302-BromothiazoleHCID 251607401-Benzyl-N-(3,4-difluorobenzyl)-6-hydroxy-2-isopropyl-1H-indole-3-carboxamide2 回

生成物 1

HCID 597622851-Benzyl-N-(3,4-difluorobenzyl)-2-isopropyl-6-(1,3-thiazol-2-yloxy)-1H-indole-3-carboxamide

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

General Procedure U. To a solution of 1-benzyl-N-(3,4-difluorobenzyl)-6-hydroxy-2-isopropyl-1H-indole-3-carboxamide (Compound 8, 12 mg, 0.028 mmol) in DMF (1 ml) was added K2CO3 (19 mg, 0.14 mmol) and 2-bromothiazole (23 mg, 0.14 mmol). The mixture was stirred at room temperature overnight and a small amount of NaOH was added. The reaction was kept stirring for 72 h, diluted with EtOAc, washed with brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes) to yield the title compound.

後処理

  1. stirringThe reaction was kept stirring for 72 h
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (0→50% EtOAc-hexanes)

出典と根拠

ORDレコード
ord-6316f0e3b36a47f98753bbe0910d7f24
出典データセット
uspto-grants-2013_09
特許番号
US08524917B2

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