Potassium Carbonate → 5-{4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]phenyl}-2-pyrrolidinone

HRID 230688Notes

Reaction equation

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

Participants

Conditions

Temperature: 190 °C

Procedure

A mixture of 5-(4-bromophenyl)-2-pyrrolidinone (81 mg, 0.34 mmol; preparation described in WO00/21958), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (64 mg, 0.34 mmol) N,N-dimethylglycine (20 mol %, 7 mg, 0.07 mmol), copper (I) iodide (10 mol %, 6.5 mg, 0.034 mmol) and potassium carbonate (0.7 mmol, 97 mg) in dimethylsulfoxide (2 ml) was stirred at 190° C. in a microwave reactor for 30 minutes. The reaction mix was cooled and partitioned between dichloromethane (5 ml) and water (5 ml). The organic layer was added to a 5 g isolute silica sep-pak column and eluted with ethyl acetate. The solvent was removed under reduced pressure to give a dark oil (161 mg) which was further purified by mass directed auto-prep (MDAP) to give the title compound as a yellow oil (17 mg, 14%).

Workup

custompreparation
additionThe reaction mix
temperaturewas cooled
custompartitioned between dichloromethane (5 ml) and water (5 ml)
additionThe organic layer was added to a 5 g isolute silica sep-pak column
washeluted with ethyl acetate
customThe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-ffbb053f73974b6fa0df1d7ef25764c8
Source dataset: uspto-grants-2009_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07566735B2

Reaction notes

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