2-Amino-5-bromobenzonitrile → 4-Amino-3'-chloro-biphenyl-3-carbonitrile

HRID 413135Notes

Reaction equation

HRID 413135 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:7](Br)=[CH:6][C:3]=1[C:4]#[N:5].[Cl:11][C:12]1[CH:13]=[C:14](B(O)O)[CH:15]=[CH:16][CH:17]=1>>[NH2:1][C:2]1[CH:9]=[CH:8][C:7]([C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:11])[CH:17]=2)=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 4297402-Amino-5-bromobenzonitrileHCID 2734323(3-Chlorophenyl)boronic acid

Product 1

HCID 97945754-Amino-3'-chloro-biphenyl-3-carbonitrile

Procedure

Prepared from 2-amino-5-bromobenzonitrile and 3-chlorophenyl boronic acid according to procedure A. Off-white solid: mp 118-119° C.; 1H-NMR (DMSO-d6) δ7.80 (d, 1H, J=2.3 Hz), 7.65-7.72 (m, 2H), 7.57 (d, 1H, J=8.0 Hz), 7.42 (t, 1H, J=7.9 Hz), 7.31 (m, 1H), 6.87 (d, 1H, J=8.7 Hz), 6.29 (br, 2H); Anal. Calc. For C13H9ClN2: C, 68.28, H, 3.97, N, 12.25. Found: C, 67.68, H, 4.06, N, 11.89.

Sources & evidence

ORD record
ord-536536fb2320486c8d01e174dcc7cca3
Source dataset
uspto-grants-2003_05
Patent number
US06566358B2

Reaction notes

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