Triethylamine → Methyl 3-(3,4-Difluorobenzylcarbamoyl)-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate

HRID 40100

反応式

HRID 40100 の反応式
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:23]([OH:25])=O)=[C:8]([C:19]([O:21][CH3:22])=[O:20])[N:9]2[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:5][CH:4]=1.C(Cl)(C(Cl)=O)=O.[F:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[F:41])[CH2:36][NH2:37].CCN(CC)CC>C(Cl)Cl.CN(C=O)C.CCOC(C)=O>[F:32][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:40]=1[F:41])[CH2:36][NH:37][C:23]([C:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C:8]=1[C:19]([O:21][CH3:22])=[O:20])=[O:25]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 1235723,4-DifluorobenzylamineHCID 597623576-Methoxy-2-(methoxycarbonyl)-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxylic Acid2 回

生成物 1

HCID 59762310Methyl 3-(3,4-Difluorobenzylcarbamoyl)-6-methoxy-1-(pyridin-2-ylmethyl)-1H-indole-2-carboxylate

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide触媒HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 6-methoxy-2-(methoxycarbonyl)-1-(pyridin-2-ylmethyl)-1H-indole-3-carboxylic acid (Compound 92, 1.59 g, 4.7 mmol) in anhydrous CH2Cl2 (50 ml) was added DMF (3 drops, catalytic amount) and (COCl)2 (2M in CH2Cl2, 5.9 ml, 11.8 mmol). The resulting mixture was stirred at room temperature for 1 h, and was concentrated in vacuo. To a solution of the crude product in CH2Cl2 (50 ml) was added 3,4-difluorobenzylamine (0.84 ml, 7.05 mmol), followed by Et3N (2.0 ml, 14.1 mmol). The reaction was stirred at room temperature for 1 h, diluted with EtOAc, washed with H2O and brine, dried over Na2SO4, and concentrated in vacuo. The residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes) to yield the title compound as a white solid.

後処理

  1. concentrationwas concentrated in vacuo
  2. stirringThe reaction was stirred at room temperature for 1 h
  3. washwashed with H2O and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography on silica gel (0→100% EtOAc-hexanes)

出典と根拠

ORDレコード
ord-21500f5beb23491a83ce2c5100e1d2b2
出典データセット
uspto-grants-2013_09
特許番号
US08524917B2

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