Hydrazine → 3-Amino-5-bromo-1H-indazole

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([CH:9]=1)[C:7]#[N:8].[NH2:11][NH2:12]>>[Br:1][C:2]1[CH:9]=[C:6]2[C:5](=[CH:4][CH:3]=1)[NH:12][N:11]=[C:7]2[NH2:8]

Participants

Reactant 2

HCID 9321Hydrazine

HCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 8179103-Amino-5-bromo-1H-indazoleYield 99.5%

Conditions

Temperature: 100 °C

Procedure

To a 250 mL round-bottom flask was added 5-bromo-2-fluorobenzonitrile (15.54 g, 77.7 mmol) and hydrazine (124 g, 3885 mmol). The reaction mixture was heated to 100° C. for 5 minutes. The hydrazine was then removed under reduced pressure to give 5-bromo-1H-indazol-3-amine (16.4 g, 99.5% yield). MS m/z: 213 (M+1).

Workup

customThe hydrazine was then removed under reduced pressure

Sources & evidence

ORD record: ord-1aeeede6f2ab47b0aa89f0d2fed652e8
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084479B2

Reaction notes

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