2-Methoxyphenylboronic acid → 3-Amino-2'methoxy-4-nitro-biphenyl-2-carbonitrile

HRID 2246904Notes

Reaction equation

HRID 2246904 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.[NH2:12][C:13]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17](Cl)[C:14]=1[C:15]#[N:16]>>[NH2:12][C:13]1[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[C:17]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[C:14]=1[C:15]#[N:16]

Participants

3

Reactant 2

HCID 27339582-Methoxyphenylboronic acidHCID 112756272-Amino-6-chloro-3-nitro-benzonitrile

Product 1

HCID 252418023-Amino-2'methoxy-4-nitro-biphenyl-2-carbonitrileYield 59%

Procedure

The title compound was prepared in 59% yield from 2-methoxy-phenylboronic acid and 2-amino-6-chloro-3-nitro-benzonitrile according to the procedure outlined for Example 5A. 1H NMR (400 MHz, CDCl3): δ 8.36 (d, 1H, J=8.8 Hz), 7.42-7.48 (m, 1H), 7.24-7.28 (m, 1H), 7.01-7.10 (m, 2H), 6.82 (br s, 2H), 6.78 (d, 1H, J=8.8 Hz), 3.86 (s, 3H). MS (ES) [m+H] calc'd for C14H11N3O3, 270; found 270.

Sources & evidence

ORD record
ord-0ba56c2e251a4693ba5ef99f26c7f461
Source dataset
uspto-grants-2010_03
Patent number
US07687638B2

Reaction notes

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