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

HRID 1661988Notes

Reaction equation

HRID 1661988 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-10c222a328d84374bbe9263e5fb2ace3
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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