Dimethylformamide → [3-(2-methyl-2H-pyrazol-3-yl)-4-trifluoromethoxy-phenyl]-carbamic acid tert-butyl ester

HRID 540615Notes

Reaction equation

HRID 540615 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[C:9]([NH:18][C:19](=[O:21])[OH:20])[CH:10]=[CH:11][C:12]=2[O:13][C:14]([F:17])([F:16])[F:15])=[CH:5][CH:4]=[N:3]1.CN(C=O)C>C(OCC)(=O)C>[C:7]([O:21][C:19](=[O:20])[NH:18][C:9]1[CH:10]=[CH:11][C:12]([O:13][C:14]([F:16])([F:17])[F:15])=[C:7]([C:6]2[N:2]([CH3:1])[N:3]=[CH:4][CH:5]=2)[CH:8]=1)([CH3:8])([CH3:12])[CH3:6]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 69687143[3-(2-methyl-2H-pyrazol-3-yl)-4-trifluoromethoxy-phenyl]-carbamic acid

Product 1

HCID 69494845[3-(2-methyl-2H-pyrazol-3-yl)-4-trifluoromethoxy-phenyl]-carbamic acid tert-butyl esterYield 89.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [3-(2-methyl-2H-pyrazol-3-yl)-4-trifluoromethoxy-phenyl]-carbamic acid tart-butyl ester (65 mg, 0.18 mmol) in DMF (1.5 mL) N-bromosuccinimide (35.6 mg, 0.2 mmol) was added at 0° C. then reaction mixture stirred at room temperature overnight. The resulting mixture was diluted with ethyl acetate, washed with brine and water. The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated to give a yellow oily residue that was subjected to a purification by flash chromatography (SiO2, Hexanes/EtOAc gradient elution) to afford [3-(2-methyl-2H-pyrazol-3-yl)-4-trifluoromethoxy-phenyl]-carbamic acid tert-butyl ester as a white solid in 89.2% yield. LCMS m/z (%)=436 (M+H 79Br, 100), 438 (M+H 81Br, 98). 1H NMR (400 MHz, CD3OD) δ: 7.79 (d, J=8.90 Hz, 1H), 7.61 (s, 1H), 7.55 (s, 1H), 7.43 (d, J=8.94 Hz, 1H), 3.73 (s, 3H), 1.55 (s, 9H).

Workup

  1. customreaction mixture
  2. washwashed with brine and water
  3. customThe organic layer was separated
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a yellow oily residue that
  8. customwas subjected to a purification by flash chromatography (SiO2, Hexanes/EtOAc gradient elution)

Sources & evidence

ORD record
ord-35eb80c785e5428fa57593b29ae297b1
Source dataset
uspto-grants-2014_10
Patent number
US08871797B2

Reaction notes

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