Pyridine → tert-butyl (1-(3-ethoxy-5-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate

HRID 1842948Notes

Reaction equation

HRID 1842948 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:7]=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[NH:5][N:4]=1.[CH2:19]([O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[C:26]([CH3:28])[CH:27]=1)[CH3:20].N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:19]([O:21][C:22]1[CH:23]=[C:24]([N:5]2[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[CH:7][C:3]([C:2]([F:1])([F:17])[F:18])=[N:4]2)[CH:25]=[C:26]([CH3:28])[CH:27]=1)[CH3:20]

Participants

6

Reactant 3

HCID 1049PyridineHCID 53216403(3-Ethoxy-5-methylphenyl)boronic acidHCID 59637276tert-butyl (3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate

Product 1

HCID 70855850tert-butyl (1-(3-ethoxy-5-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamateYield 94%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl (3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate (251 mg, 0.947 mmol, 1 equiv.), 3-ethoxy-5-methylphenylboronic acid (341 mg, 1.89 mmol, 2 equiv.) and copper acetate (259 mg, 1.42 mmol, 1.5 equiv.) in dichloromethane was added pyridine (151 mg, 0.151 mL, 1.89 mmol, 2 equiv) and the mixture was stirred for 2 d at room temperature. The reaction mixture was filtered over silica gel, the filter cake was washed with 250 mL of dichloromethane and the filtrate was evaporated to give tert-butyl (1-(3-ethoxy-5-methylphenyl)-3-(trifluoromethyl)-1H-pyrazol-5-yl)methylcarbamate (354 mg, 94%).

Workup

  1. filtrationThe reaction mixture was filtered over silica gel
  2. washthe filter cake was washed with 250 mL of dichloromethane
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-44304d8b0c1b4af5aed82ef9ba05211d
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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