(4-Chloro-3-methylphenyl)boronic acid → 2-(3-Nitro-6-propylaminophenyl)-5-(3-methyl-4-chlorophenyl)benzoxazole

HRID 722660Notes

Reaction equation

HRID 722660 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][C:20](Br)=[CH:19][C:17]=3[N:18]=2)[C:7]([NH:10][CH2:11][CH2:12][CH3:13])=[CH:8][CH:9]=1)([O-:3])=[O:2].[CH3:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][C:30]=1[Cl:31]>>[N+:1]([C:4]1[CH:5]=[C:6]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][C:20]([C:27]4[CH:28]=[CH:29][C:30]([Cl:31])=[C:25]([CH3:24])[CH:26]=4)=[CH:19][C:17]=3[N:18]=2)[C:7]([NH:10][CH2:11][CH2:12][CH3:13])=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

3

Reactant 2

HCID 3786632(4-Chloro-3-methylphenyl)boronic acidHCID 53038022-(5-bromo-1,3-benzoxazol-2-yl)-4-nitro-N-propylaniline

Product 1

HCID 218843562-(3-Nitro-6-propylaminophenyl)-5-(3-methyl-4-chlorophenyl)benzoxazole

Procedure

Prepared by the method of Example 15d), from 2-(3-nitro-6-propylaminophenyl)-5-bromobenzoxazole (400 mg, 1.59 mmol) and 3-methyl-4-chlorophenylboronic acid (271 mg, 1.59 mmol) the subtitle compound was obtained (230 mg, 34%). The product was used directly in the next step without purification.

Sources & evidence

ORD record
ord-a97a2b3cda264dfe995f4eef17468da3
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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