(4-Methoxyphenyl)hydrazine → 5-Bromo-1-(4-methoxy-phenyl)-1H-indazole

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.Br[C:12]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][C:13]=1[CH:14]=O>>[Br:20][C:17]1[CH:16]=[C:13]2[C:12](=[CH:19][CH:18]=1)[N:9]([C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[N:10]=[CH:14]2

Participants

Reactant 2

HCID 77023(4-Methoxyphenyl)hydrazine

HCID 135400692,5-Dibromobenzaldehyde

Product 1

HCID 574213515-Bromo-1-(4-methoxy-phenyl)-1H-indazole

Procedure

In analogy to Example 187, step 1, 4-methoxyphenylhydrazine was reacted with 2,5-dibromobenzaldehyde to give the title compound as a light brown solid. MS (m/e)=303.0 [M+H+].

Sources & evidence

ORD record: ord-95b6baee070b4023b78896d067c510fa
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143280B2

Reaction notes

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