(3,5-Difluorophenyl)boronic acid → 2-(3-Nitro-4-methoxyphenyl)-5-(3,5-difluorophenyl)benzoxazole

HRID 722514Notes

Reaction equation

HRID 722514 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18](Br)=[CH:17][C:15]=3[N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])([O-:3])=[O:2].[F:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[C:27]([F:29])[CH:28]=1>>[N+:1]([C:4]1[CH:5]=[C:6]([C:12]2[O:13][C:14]3[CH:20]=[CH:19][C:18]([C:25]4[CH:24]=[C:23]([F:22])[CH:28]=[C:27]([F:29])[CH:26]=4)=[CH:17][C:15]=3[N:16]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 2734338(3,5-Difluorophenyl)boronic acidHCID 218843422-(3-Nitro-4-methoxyphenyl)-5-bromobenzoxazole

Product 1

HCID 218843112-(3-Nitro-4-methoxyphenyl)-5-(3,5-difluorophenyl)benzoxazole

Procedure

Prepared by the method of Example 15d), from 2-(3-nitro-4-methoxyphenyl)-5-bromobenzoxazole (200 mg, 0.57 mmol) and 3,5-difluorophenylboronic acid (136 mg, 0.86 mmol) the subtitle compound was obtained, (120 mg, 64%). 1H NMR (DMSO) δ 8.70(d, 1H), 8.52(dd, 1H), 8.26(d, 1H), 7.96(d, 1H), 7.88(dd, 1H), 7.69(d, 1H), 7.61(dd, 2H), 7.33(tt, 1H), 4.12(s, 3H). MS 383 m/z (M+H)+.

Sources & evidence

ORD record
ord-aec923def7f549d6822c6d22ebbe206a
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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