(2R)-2-(Trifluoromethyl)pyrrolidine → (R)-methyl 2-(4-fluorophenyl)-3-(2-(trifluoromethyl)pyrrolidin-1-yl)quinoxaline-6-carboxylate
Reaction equation
Cl[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[F:23][C:24]([F:31])([F:30])[C@H:25]1[CH2:29][CH2:28][CH2:27][NH:26]1>CS(C)=O>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:3]2[C:2]([N:26]3[CH2:27][CH2:28][CH2:29][C@@H:25]3[C:24]([F:31])([F:30])[F:23])=[N:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=3)[N:4]=2)=[CH:17][CH:18]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
To a solution of methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (270 mg, 0.85 mmol) in DMSO (1 mL) was added (R)-2-(trifluoromethyl)pyrrolidine (275 mg, 1.99 mmol). The resulting solution was stirred 7 days at 130° C. and then evaporated in vacuo. The residue was diluted with petroleum ether (15 mL) and filtered. The filtrate was concentrated and purified by a silica gel column chromatography with 2%-10% ethyl acetate in petroleum ether to afford (R)-methyl 2-(4-fluorophenyl)-3-(2-(trifluoromethyl)pyrrolidin-1-yl)quinoxaline-6-carboxylate as a yellow solid (35 mg, crude).
Workup
- customevaporated in vacuo
- additionThe residue was diluted with petroleum ether (15 mL)
- filtrationfiltered
- concentrationThe filtrate was concentrated
- custompurified by a silica gel column chromatography with 2%-10% ethyl acetate in petroleum ether
Sources & evidence
- ORD record
- ord-7d9db9235cc0473298fe6487a8ca74a4
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916561B2
Reaction notes
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