Water → (3-Trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetic acid tert-butyl ester

HRID 1162735Notes

Reaction equation

HRID 1162735 reaction equation
[H-].[Na+].[F:3][C:4]([F:15])([F:14])[C:5]1[C:13]2[CH2:12][CH2:11][CH2:10][CH2:9][C:8]=2[NH:7][N:6]=1.Br[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].O>CN(C=O)C>[C:21]([O:20][C:18](=[O:19])[CH2:17][N:7]1[C:8]2[CH2:9][CH2:10][CH2:11][CH2:12][C:13]=2[C:5]([C:4]([F:3])([F:14])[F:15])=[N:6]1)([CH3:24])([CH3:23])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 28028633-(Trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole

Product 1

HCID 68647733(3-Trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% [w/w] dispersion in mineral oil, 632 mg, 15.8 mmol) was added portionwise to a stirred solution of 4,5,6,7-tetrahydro-3-(trifluoromethyl)-indazole (3.00 g, 15.8 mmol) in DMF (60 mL), and the mixture stirred at RT for 30 min. Tert-butyl bromoacetate (2.33 mL, 15.8 mmol) was added and the reaction mixture stirred at 80° C. for 2 h, and allowed to cool to RT. Water (50 mL) was added and the resulting solution extracted with EtOAc (3×200 mL), washed with water (200 mL), brine (200 mL), dried over sodium sulfate, and concentrated in vacuo to afford (3-Trifluoromethyl-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid tert-butyl ester.

Workup

  1. stirringthe reaction mixture stirred at 80° C. for 2 h
  2. temperatureto cool to RT
  3. extractionthe resulting solution extracted with EtOAc (3×200 mL)
  4. washwashed with water (200 mL), brine (200 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ad775a7234814c00a7655a581e4b9ef6
Source dataset
uspto-grants-2010_10
Patent number
US07820707B2

Reaction notes

Loading…