3-Aminobenzonitrile → 4-(4-bromo-2-methylphenyl)-N-(3-cyanophenyl)butanamide

HRID 735639Notes

Reaction equation

HRID 735639 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17](S(CC)(=O)=O)=[C:16]([C:25]#[N:26])[CH:15]=2)=[O:12])=[CH:4][CH:3]=1.Br[C:28]1C=CC(CCCC(O)=O)=C(C)C=1.NC1C=C(C=CC=1)C#N>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:25]#[N:26])[CH:15]=2)=[O:12])=[C:6]([CH3:28])[CH:7]=1

Participants

4

Reactant 3

HCID 167023-AminobenzonitrileHCID 578426164-(4-Bromo-2-methylphenyl)butanoic acidHCID 578426674-(4-Bromophenyl)-N-(3-cyano-4-(ethylsulfonyl)phenyl)butanamide

Product 1

HCID 578427454-(4-bromo-2-methylphenyl)-N-(3-cyanophenyl)butanamideYield 76%

Procedure

Using a procedure analogous to that used to prepare 6C, 55B (216 mg, 0.84 mmol) was reacted with 3-aminobenzonitrile to afford 55C (228 mg, 76%) as a solid. MS (ESI) m/z 358.1 (M+H)+.

Sources & evidence

ORD record
ord-8c54c5559cff455db3643cff6f0ef84f
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

Loading…