Thiophene-3-boronic acid → 2-(3-Nitro-4-(3-thienyl)phenyl)-5-phenylbenzoxazole

HRID 722619Notes

Reaction equation

HRID 722619 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:16][C:14]=3[N:15]=2)[CH:7]=[CH:8][C:9]=1Cl)([O-:3])=[O:2].[S:26]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27]1>>[N+:1]([C:4]1[CH:5]=[C:6]([C:11]2[O:12][C:13]3[CH:19]=[CH:18][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[CH:16][C:14]=3[N:15]=2)[CH:7]=[CH:8][C:9]=1[C:28]1[CH:29]=[CH:30][S:26][CH:27]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 581760Thiophene-3-boronic acidHCID 218843272-(3-Nitro-4-chlorophenyl)-5-phenylbenzoxazole

Product 1

HCID 218846172-(3-Nitro-4-(3-thienyl)phenyl)-5-phenylbenzoxazole

Procedure

Prepared by the method of Example 15d), from 2-(3-nitro-4-chlorophenyl)-5-phenylbenzoxazole (177 mg, 0.51 mmol) and thiophene-3-boronic acid (97 mg, 0.76 mmol) the subtitle compound was obtained (150 mg, 74%). 1H NMR (DMSO) δ 8.67(d, 1H), 8.48(dd, 1H), 8.12(d, 1H), 7.91(m, 2H), 7.83(m, 1H), 7.79–7.77(m, 4H), 7.51(m, 2H), 7.40(t, 1H), 7.22(dd, 1H).

Sources & evidence

ORD record
ord-519de73744d64d48ad71c801f854f952
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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