Water → 4-Bromo-3-isopropyl-1H-indazole

HRID 1091923Notes

Reaction equation

HRID 1091923 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](F)[C:3]=1[C:9](=O)[CH:10]([CH3:12])[CH3:11].[NH2:14][NH2:15].O>C(O)CO>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]2[C:3]=1[C:9]([CH:10]([CH3:12])[CH3:11])=[N:14][NH:15]2

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 665895481-(2-Bromo-6-fluorophenyl)-2-methylpropan-1-one

Product 1

HCID 1784404044-Bromo-3-isopropyl-1H-indazole

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1-(2-bromo-6-fluoro-phenyl)-2-methyl-propan-1-one (1.1 g, 4.5 mmol) and anhydrous hydrazine (0.17 mL, 5.4 mmol) in ethylene glycol (10 mL) is heated for 16 h at 160° C. Water is added and the mixture is extracted with CH2Cl2. The combined extracts are dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography to yield 4-bromo-3-isopropyl-1H-indazole. 1H NMR (CDCl3) 10.1 (br s, 1H), 7.38 (d, 1H), 7.32 (d, 1H), 7.17 (t, 1H), 3.99 (m, 1H), 1.43 (d, 6H).

Workup

  1. extractionthe mixture is extracted with CH2Cl2
  2. dry with materialThe combined extracts are dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-bffe12baf6aa4176a42d9ae1327c714c
Source dataset
uspto-grants-2012_03
Patent number
US08129395B2

Reaction notes

Loading…