Diethyl Ether → 1-Acetyl-5-(acetyloxy)-6-bromo-1H-indazole

HRID 2195504Notes

Reaction equation

HRID 2195504 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[OH:11].C([O:14][CH2:15][CH3:16])C.[C:17](OC(=O)C)(=[O:19])[CH3:18]>>[C:17]([O:11][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[Br:1])[N:8]([C:15](=[O:14])[CH3:16])[N:7]=[CH:6]2)(=[O:19])[CH3:18]

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 591599466-Bromo-1H-indazol-5-ol

Product 1

HCID 667671231-Acetyl-5-(acetyloxy)-6-bromo-1H-indazoleYield 98%

Conditions

Temperature
110 °C

Procedure

A mixture of 6-bromo-5-hydroxy-1H-indazole (25 g, 117 mmol) in acetic acid anhydride (75 mL) is heated at 110° C. with stirring for 2 hours. After it is cooled, diethyl ether (100 mL) is added. The precipitate is collected by filtration, washed with diethyl ether (30 mL), and dried under vacuum to afford the product (34 g, 98% yield). MS (m/z): 297.0 (M+H).

Workup

  1. temperatureAfter it is cooled
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with diethyl ether (30 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-1245610d97b54ce0b13512a909201393
Source dataset
uspto-grants-2012_12
Patent number
USRE043878E1

Reaction notes

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