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

HRID 1630795Notes

Reaction equation

HRID 1630795 reaction equation
[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]

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-b9a8a7bbbde34e7c941e34e99680cdeb
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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