Potassium Carbonate → HCID 56954419, compound

HRID 871689Notes

Reaction equation

HRID 871689 reaction equation
[C:1]1([N:7]2[C:11]([NH2:12])=[CH:10][C:9]([C:13]([CH3:19])([CH3:18])[C:14]([F:17])([F:16])[F:15])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28]>C(Cl)Cl>[C:1]1([N:7]2[C:11]([NH:12][C:27](=[O:28])[O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:10][C:9]([C:13]([CH3:19])([CH3:18])[C:14]([F:16])([F:17])[F:15])=[N:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 56954316HCID 56954316, compound

Product 1

HCID 56954419HCID 56954419, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-phenyl-3-(1,1,1-trifluoro-2-methylpropan-2-yl)-1H-pyrazol-5-amine (590 mg, 2.2 mmol) and potassium carbonate (304 mg, 2.85 mmol) in anhydrous DCM (5.2 ml) was added dropwise phenyl chloroformate (0.30 ml, 2.4 mmol) as a solution in DCM (2.5 ml). The reaction mixture was stirred at rt overnight, then filtered and concentrated under reduced pressure. The crude was purified by silica gel chromatography (hexane/ethyl acetate 35%) to afford phenyl 1-phenyl-3-(1,1,1-trifluoro-2-methylpropan-2-yl)-1H-pyrazol-5-ylcarbamate (748 mg, 87%) as a solid. 1H NMR (300 MHz, CDCl3) δ 1.60 (s, 6H), 6.65 (brs, 1H), 7.02-7.55 (m, 11H); LC-MS (ESI) m/z 390 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated under reduced pressure
  3. customThe crude was purified by silica gel chromatography (hexane/ethyl acetate 35%)

Sources & evidence

ORD record
ord-9087976a25364818ad9d02b7881e0be3
Source dataset
uspto-grants-2015_03
Patent number
US08969587B2

Reaction notes

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