N,N-Dimethylglycine → 4-[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]benzonitrile

HRID 1988620Notes

Reaction equation

I[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[F:10][C:11]([F:22])([F:21])[C:12]1[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[NH:14][N:13]=1.CN(C)CC(O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.C(OCC)(=O)C.[Cu-]=O>[F:22][C:11]([F:10])([F:21])[C:12]1[C:20]2[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=2[N:14]([C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[N:13]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 4-iodobenzonitrile (2.41 g, 10.5 mmol), 3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazole (2.0 g, 10.5 mmol), copper (I) oxide (20 mol %, 2.1 mmol, 300 mg), N,N-dimethylglycine (10.5 mmol, 1.082 g), and cesium carbonate (21 mmol, 6.84 g) in dimethylsulfoxide (5 ml) was heated in an oil bath at 130° C. under argon for 4 h. The reaction mixture was diluted with ethyl acetate. Solid filtered off through kieselguhr. The filtrate was partitioned between ethyl acetate and water. The organic layer was separated and dried over sodium sulphate. The solvent was removed by rotary evaporation and triturated with diethyl ether to give the title compound as a light brown solid (1.812 g, 59.5%).

Workup

filtrationSolid filtered off through kieselguhr
customThe filtrate was partitioned between ethyl acetate and water
customThe organic layer was separated
dry with materialdried over sodium sulphate
customThe solvent was removed by rotary evaporation
customtriturated with diethyl ether

Sources & evidence

ORD record: ord-0ba49a735d1741e3a4cb699a38154399
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642256B2

Reaction notes

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