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

HRID 606301Notes

Reaction equation

HRID 606301 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 hours 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-212dace8fbdc4bcbb754d119ccc848a2
Source dataset
uspto-grants-2011_03
Patent number
US07915288B2

Reaction notes

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