Trifluoroacetic anhydride → (S)-2-(4-Fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carbonitrile

HRID 1405308Notes

Reaction equation

HRID 1405308 reaction equation
C([NH:5][C:6]([C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=1)[C:12]([N:25]1[CH2:29][CH2:28][CH2:27][C@@H:26]1[CH3:30])=[N:11]2)=O)(C)(C)C.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>ClCCl>[F:24][C:21]1[CH:22]=[CH:23][C:18]([C:13]2[C:12]([N:25]3[CH2:29][CH2:28][CH2:27][C@@H:26]3[CH3:30])=[N:11][C:10]3[C:15](=[CH:16][CH:17]=[C:8]([C:6]#[N:5])[CH:9]=3)[N:14]=2)=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 70654210(S)-N-tert-butyl-2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxamide

Product 1

HCID 70654208(S)-2-(4-Fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)—N-tert-butyl-2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxamide (160 mg, crude) in dichloromethane (30 mL) was added TFAA (4 mL). The resulting solution was stirred overnight at room temperature and then quenched by the addition water (100 mL), adjusted to pH 7 with sodium bicarbonate, and extracted with dichloromethane (3×30 mL). The organic layers combined and dried over anhydrous sodium sulfate and concentrated in vacuo to (S)-2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carbonitrile as a yellow solid (100 mg, 53%).

Workup

  1. customquenched by the addition water (100 mL)
  2. extractionextracted with dichloromethane (3×30 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo to (S)-2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carbonitrile as a yellow solid (100 mg, 53%)

Sources & evidence

ORD record
ord-a5c24eb28f8f4ea594392844e9c5980e
Source dataset
uspto-grants-2014_12
Patent number
US08916561B2

Reaction notes

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