1-Butanol → (S)-butyl 2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

HRID 717024Notes

Reaction equation

HRID 717024 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.[CH3:23][C@H:24]1[CH2:28][CH2:27][CH2:26][NH:25]1.[CH2:29](O)[CH2:30][CH2:31]C>>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:3]2[C:2]([N:25]3[CH2:26][CH2:27][CH2:28][C@@H:24]3[CH3:23])=[N:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH2:15][CH2:29][CH2:30][CH3:31])=[O:13])[CH:9]=3)[N:4]=2)=[CH:17][CH:18]=1

Participants

4

Reactant 3

HCID 2631-ButanolHCID 6999702(2S)-2-methylpyrrolidineHCID 77231184Methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate

Product 1

HCID 68063092(S)-butyl 2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate

Conditions

Temperature
110 °C

Procedure

Into a 10-mL sealed tube, was placed methyl 3-chloro-2-(4-fluorophenyl)quinoxaline-6-carboxylate (150 mg, 0.47 mmol, 1.00 equiv), (S)-2-methylpyrrolidine (403 mg, 4.74 mmol, 9.99 equiv), butan-1-ol (2 mL). The resulting solution was stirred overnight at 110° C. in an oil bath. The resulting mixture was concentrated under vacuum. This resulted in 150 mg (crude) of (S)-butyl 2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate as a yellow solid.

Workup

  1. customInto a 10-mL sealed tube
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. customThis resulted in 150 mg (crude) of (S)-butyl 2-(4-fluorophenyl)-3-(2-methylpyrrolidin-1-yl)quinoxaline-6-carboxylate as a yellow solid

Sources & evidence

ORD record
ord-61c638fc1b7c455d812a093be0ee7841
Source dataset
uspto-grants-2015_11
Patent number
US09193693B2

Reaction notes

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