4-Chlorophenylboronic acid → HCID 22504967, compound

HRID 1813974Notes

Reaction equation

HRID 1813974 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[C:4]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[O:16][CH3:17])[N:3]=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1>>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:22]2[CH:23]=[CH:24][C:19]([Cl:18])=[CH:20][CH:21]=2)[CH:5]=[C:4]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[O:16][CH3:17])[N:3]=1

Participants

3

Reactant 2

HCID 742994-Chlorophenylboronic acidHCID 22504957HCID 22504957, compound

Product 1

HCID 22504967HCID 22504967, compoundYield 56%

Procedure

Following the method described in Example 1, 2-chloro-6-(5-chloro-2-methoxy-phenyl)-pyridin-4-yl-amine and 4-chloro-phenylboronic acid gave 2-chloro-6-(5-chloro-2-methoxy-phenyl)-pyridin-4-yl-(4-chloro-phenyl)-amine in 56% yield. 1H NMR (acetone-d6) δ 3.92(s, 3H, CH3), 6.86 (d, 1H, J=8.9 Hz, Ar), 6.90 (t, 1H, J=1.9 Hz, Ar), 7.18 (d, 1H, J=8.9 Hz, Ar), 7.20 (d, 1H, J=8.9 Hz, Ar), 7.36 (d, 2H, J=8.9 Hz, Ar), 7.41 (dd, 1H, J=8.8 Hz, J=2.8 Hz, Ar), 7.46 (d, 2H, J=8.9 Hz, Ar), 7.72 (t, 1H, J=1.9 Hz, Ar), 7.95 (d, 1H, J=2.8 Hz, Ar).

Sources & evidence

ORD record
ord-8936c9d02ae34eb49d66d317db065e9e
Source dataset
uspto-grants-2005_04
Patent number
US06875781B2

Reaction notes

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