Potassium Carbonate → 1-(difluoromethyl)-4-ethynyl-1H-pyrazole

HRID 2205945Notes

Reaction equation

HRID 2205945 reaction equation
[F:1][CH:2]([F:14])[N:3]1[CH:7]=[C:6]([C:8]#[C:9][Si](C)(C)C)[CH:5]=[N:4]1.C(=O)([O-])[O-].[K+].[K+]>CO>[F:1][CH:2]([F:14])[N:3]1[CH:7]=[C:6]([C:8]#[CH:9])[CH:5]=[N:4]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 682906451-(Difluoromethyl)-4-((trimethylsilyl)ethynyl)-1H-pyrazole

Product 1

HCID 867063321-(difluoromethyl)-4-ethynyl-1H-pyrazoleYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1-(Difluoromethyl)-4-((trimethylsilyl)ethynyl)-1H-pyrazole (Preparation 151, 413 mg, 1.9 mmole) was stirred with methanol (4 mL). Potassium carbonate (17 mg) was added and stirred at room temperature for 50 minutes. The solvent was evaporated and the residue was filtered in dichloromethane through a short pad of silica to afford the title compound (187 mg 1.31 mmole 72%). 1H-NMR (CDCl3, 500 MHz): δ 3.08 (s, 1H), 7.17 (t, J=60.5 Hz, 1H), 7.75 (s, 1H), 7.97 (s, 1H).

Workup

  1. customThe solvent was evaporated
  2. filtrationthe residue was filtered in dichloromethane through a short pad of silica

Sources & evidence

ORD record
ord-a7eac286688e4b9d9596b38ba463631b
Source dataset
uspto-grants-2016_06
Patent number
US09371319B2

Reaction notes

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