Hydrogen Bromide → 5-(Bromomethyl)-1H-indazole--hydrogen bromide (1/1)

HRID 1634078Notes

Reaction equation

HRID 1634078 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13]OC(=O)C)=[CH:10][CH:11]=2)[CH:6]=[N:5]1)(=O)C.[BrH:18]>>[BrH:18].[Br:18][CH2:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[NH:4][N:5]=[CH:6]2

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 107995691-Acetyl-5-(acetoxymethyl)indazole

Product 1

HCID 226614415-(Bromomethyl)-1H-indazole--hydrogen bromide (1/1)

Procedure

A suspension of 1-acetyl-5-(acetoxymethyl)indazole (106) (3.0 g, 13 mmol) in aqueous hydrobromic acid (15 mL, 226 mmol) was stirred at room temperature for 25 hours. The solid was collected on a Buchner funnel and dried under vacuum for 12 hours. The filtrate was stirred at room temperature for additional 24 hours and more solid was collected. After drying under vacuum, title compound was obtained as a yellow solid (107, 3.48 g, 92%) which was used in the next synthesis step without further purification. 1H NMR (CDCl3) δ 4.88 (s, 2H), 7.43 (d, 1H, J=8.8), 7.56 (d, 1H, J=8.8 Hz), 7.87 (s, 1H), 8.10 (s, 1H).

Workup

  1. customThe solid was collected on a Buchner funnel
  2. customdried under vacuum for 12 hours
  3. stirringThe filtrate was stirred at room temperature for additional 24 hours
  4. custommore solid was collected
  5. customAfter drying under vacuum

Sources & evidence

ORD record
ord-3dcc0fd4adef41dd8acf0cdecc4f1b99
Source dataset
uspto-grants-2003_01
Patent number
US06506754B1

Reaction notes

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