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

HRID 722500Notes

Reaction equation

HRID 722500 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][CH:27]=[CH:26][C:25]=1B(O)O>>[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:26]=[CH:27][CH:28]=[CH:29][C:24]=4[O:23][CH3:22])=[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 27339582-Methoxyphenylboronic acidHCID 218843422-(3-Nitro-4-methoxyphenyl)-5-bromobenzoxazole

Product 1

HCID 218846432-(3-Nitro-4-methoxyphenyl)-5-(2-methoxyphenyl)benzoxazole

Procedure

Prepared by the method of Example 15d), from 2-(3-nitro-4-methoxyphenyl)-5-bromobenzoxazole (200 mg, 0.57 mmol) and 2-methoxyphenylboronic acid (130 mg, 0.85 mmol) the subtitle compound was obtained (163 mg, 76%). 1H NMR (CDCl3) δ 8.75(d, 1H), 8.45(dd, 1H), 7.93(d, 1H), 7.61(d, 1H), 7.54(dd, 1H), 7.39–7.34(m, 2H), 7.25(d, 1H), 7.09–7.01(m, 2H), 4.07(s, 3H), 3.83(s, 3H).

Sources & evidence

ORD record
ord-b4bab884d44346019f71933548d683b3
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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