Potassium Carbonate → HCID 24827138, compound

HRID 230666Notes

Reaction equation

HRID 230666 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:10])=[CH:5][CH:4]=1.[F:16][C:17]([F:28])([F:27])[C:18]1[C:26]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]=2[NH:20][N:19]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:11]1([C:9]([C:6]2[CH:7]=[CH:8][C:3]([CH2:2][N:20]3[C:21]4[CH2:22][CH2:23][CH2:24][CH2:25][C:26]=4[C:18]([C:17]([F:16])([F:28])[F:27])=[N:19]3)=[CH:4][CH:5]=2)=[O:10])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 28028633-(Trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazoleHCID 57762815HCID 57762815, compound

Product 1

HCID 24827138HCID 24827138, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 1-{[4-(bromomethyl)phenyl]carbonyl}pyrrolidine (84 mg, 0.31 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (60 mg, 0.32 mmol), and potassium carbonate (87 mg, 0.63 mmol) in N,N-dimethylformamide (2 ml) was stirred at 140° C. in a microwave reactor for 10 minutes. The reaction mixture was cooled and partitioned between dichloromethane and water. The organic layer was dried over sodium sulphate and reduced to minimum volume under reduced pressure. The crude product was purified using mass directed auto-prep to give the title compound as a pale yellow oil (63 mg, 54%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. custompartitioned between dichloromethane and water
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. customThe crude product was purified

Sources & evidence

ORD record
ord-986942a66ada4d988f713bf964585912
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Reaction notes

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