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

HRID 593524

반응식

HRID 593524 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 142844-(Dimethylamino)pyridine촉매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-5c588d7e1c4d4c29a12ce7a92ddb3ea8
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242963B2

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