(4-Methoxyphenyl)boronic acid → 2-(3-Nitro-4-methoxyphenyl)-5-(4-methoxyphenyl)benzoxazole

HRID 722506Notes

Reaction equation

HRID 722506 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].[CH3:22][O:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=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:27]4[CH:28]=[CH:29][C:24]([O:23][CH3:22])=[CH:25][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 201262(4-Methoxyphenyl)boronic acidHCID 218843422-(3-Nitro-4-methoxyphenyl)-5-bromobenzoxazole

Product 1

HCID 218843412-(3-Nitro-4-methoxyphenyl)-5-(4-methoxyphenyl)benzoxazole

Procedure

Prepared by the method of Example 15d), from 2-(3-nitro-4-methoxyphenyl)-5-bromobenzoxazole (200 mg, 0.57 mmol) and 4-methoxyphenylboronic acid (129 mg, 0.85 mmol) the subtitle compound was obtained (193 mg, 60%). 1H NMR (DMSO) δ 8.63(d, 1H), 8.45(dd, 1H), 7.99(d, 1H), 7.83(d, 1H), 7.67(d, 3H), 7.62(d, 1H), 7.05(d, 2H), 4.05(s, 3H), 3.81(s, 3H).

Sources & evidence

ORD record
ord-e767915570494ea997799de55c7e3ac1
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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