(2H-1,3-benzodioxol-5-yl)boronic acid → 2-(3-Nitro-6-propylaminophenyl)-5-(3,4-methylenedioxyphenyl)benzoxazole

HRID 722656Notes

Reaction equation

HRID 722656 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].[CH2:24]1[O:32][C:31]2[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][C:26]=2[O:25]1>>[N+:1]([C:4]1[CH:5]=[C:6]([C:14]2[O:15][C:16]3[CH:22]=[CH:21][C:20]([C:29]4[CH:28]=[CH:27][C:26]5[O:25][CH2:24][O:32][C:31]=5[CH:30]=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 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 53038022-(5-bromo-1,3-benzoxazol-2-yl)-4-nitro-N-propylaniline

Product 1

HCID 695851072-(3-Nitro-6-propylaminophenyl)-5-(3,4-methylenedioxyphenyl)benzoxazole

Procedure

Prepared by the method of Example 15d), from 2-(3-nitro-6-propylaminophenyl)-5-bromobenzoxazole (400 mg, 1.59 mmol) and 3,4-methylenedioxyphenylboronic acid (264 mg, 1.59 mmol) the subtitle compound was obtained (337 mg, 51%). The product was used directly in the next step without purification.

Sources & evidence

ORD record
ord-6b49128cb8404e61a4086c99d8bb3add
Source dataset
uspto-grants-2006_11
Patent number
US07138425B2

Reaction notes

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