Bromoacetonitrile → 9-Benzyl-4-cyanomethyloxy-2-methoxycarbazole-5-carboxamide

HRID 567375Notes

Reaction equation

HRID 567375 reaction equation
[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([C:21]([NH2:23])=[O:22])[C:15]=2[C:14]2[C:9]1=[CH:10][C:11]([O:25][CH3:26])=[CH:12][C:13]=2[OH:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:30][C:31]#[N:32]>CN(C=O)C.C1COCC1.CCOC(C)=O>[CH2:1]([N:8]1[C:20]2[CH:19]=[CH:18][CH:17]=[C:16]([C:21]([NH2:23])=[O:22])[C:15]=2[C:14]2[C:9]1=[CH:10][C:11]([O:25][CH3:26])=[CH:12][C:13]=2[O:24][CH2:30][C:31]#[N:32])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 11534BromoacetonitrileHCID 24758Sodium hydrideHCID 227403229-Benzyl-5-hydroxy-7-methoxycarbazole-4-carboxamide

Product 1

HCID 101569139-Benzyl-4-cyanomethyloxy-2-methoxycarbazole-5-carboxamideYield 63%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 9-benzyl-5-hydroxy-7-methoxycarbazole-4-carboxamide (0.75 g, 2.17 mmol) in DMF (76 ml) and THF (16 ml) and added 60% NaH (0.11 g, 2.71 mmol). After 15 min bromoacetonitrile (0.20 ml, 2.93 mmol) was added and the reaction was allowed to stir for 4 h. The reaction was diluted with EtOAc, extracted with water, then brine, dried (Na2SO4), and chromatographed on silica gel using a CH2Cl2-EtOAc-methanol gradient to give the titled compound (0.52 g, 63%). MS (ES+) 386

Workup

  1. extractionextracted with water
  2. dry with materialbrine, dried (Na2SO4)
  3. customchromatographed on silica gel using a CH2Cl2-EtOAc-methanol gradient

Sources & evidence

ORD record
ord-4de52c1332124f508e64c91a7845f900
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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