Carbon tetrabromide → HCID 54297830, compound

HRID 1934701Notes

Reaction equation

HRID 1934701 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([C:22]1[CH:23]=[CH:24][C:25]([NH:42][C@@H:43]([CH3:46])[CH2:44]O)=[C:26]([CH:41]=1)[C:27]([NH:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=1)=[O:28])#[N:21].C(Br)(Br)(Br)[Br:48]>ClCCl>[Br:48][CH2:44][C@@H:43]([NH:42][C:25]1[CH:24]=[CH:23][C:22]([C:20]#[N:21])=[CH:41][C:26]=1[C:27]([NH:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[C:33]([O:39][CH3:40])[CH:32]=1)=[O:28])[CH3:46]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 54513542HCID 54513542, compound

Product 1

HCID 54297830HCID 54297830, compoundYield 68.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triphenylphosphine (156 mg) was added to a mixture of (S)-5-cyano-N-(3,4-dimethoxybenzyl)-2-(2-hydroxy-1-methylethylamino)benzamide (200 mg) and carbontetrabromide (215 mg) in dichloromethane (4 mL), and the mixture was stirred for an hour at ambient temperature. After evaporation of the solvent, the residue was subjected to a silica gel column chromatography eluting with a mixture of chloroform and ethyl acetate (9:1) to give (S)-2-(2-bromo-1-methylethylamino)-5-cyano-N-(3,4-dimethoxybenzyl)benzamide (161 mg) as a solid substance.

Workup

  1. customAfter evaporation of the solvent
  2. washeluting with a mixture of chloroform and ethyl acetate (9:1)

Sources & evidence

ORD record
ord-503f954af941415c9759405e6d57ccb1
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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