Water → 4-(5-Cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid tert-butyl ester

HRID 593524ノート

反応式

HRID 593524 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][C:12]([C:16]#[N:17])=[CH:11][CH:10]=3)[CH:2]=1.C(O[C:23]([C:25]1[CH:33]=[CH:32][C:28]([C:29]([OH:31])=O)=[CH:27][CH:26]=1)=[O:24])CCC.C1CCC(N=C=N[CH:43]2[CH2:48][CH2:47]CCC2)CC1.[OH2:49].[CH3:50]N(C=O)C>CN(C1C=CN=CC=1)C>[C:48]([O:49][C:23](=[O:24])[C:25]1[CH:26]=[CH:27][C:28]([C:29]([N:8]2[C:9]3[C:14](=[CH:13][C:12]([C:16]#[N:17])=[CH:11][CH:10]=3)[CH:15]=[C:7]2[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[O:31])=[CH:32][CH:33]=1)([CH3:47])([CH3:43])[CH3:50]

参加物

7

反応物 5

HCID 962WaterHCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 745571,4-Benzenedicarboxylic acid, 1-butyl esterHCID 445541352-pyridin-3-yl-1H-indole-5-carbonitrile

生成物 1

HCID 582157224-(5-Cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 142844-(Dimethylamino)pyridine触媒

実験手順

To 2-pyridin-3-yl-1H-indole-5-carbonitrile (575 mg, 2.62 mmol), 4-(butoxycarbonyl)benzoic acid (700 mg, 3.15 mmol) and DMAP (780 mg, 3.93 mmol) in DMF (30 mL) is added DCC (811 mg, 3.93 mmol). The reaction is stirred for 3 days and the mixture is poured into water (50 mL) and extracted with ethyl acetate, dried over Na2SO4 and concentrated. The residue is purified by silica gel flash chromatography (ethyl acetate-heptane gradient) to give 4-(5-cyano-2-pyridin-3-yl-indole-1-carbonyl)-benzoic acid tert-butyl ester as a white solid. MS (ESI) m/z 424 (M+H)+.

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue is purified by silica gel flash chromatography (ethyl acetate-heptane gradient)

出典と根拠

ORDレコード
ord-5c588d7e1c4d4c29a12ce7a92ddb3ea8
出典データセット
uspto-grants-2016_01
特許番号
US09242963B2

反応ノート

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