Pyridine → HCID 69083478, compound

HRID 1852898Notes

Reaction equation

HRID 1852898 reaction equation
[CH3:1][C:2]1([CH3:24])[C:11]2[N:10]=[CH:9][CH:8]=[N:7][C:6]=2[C:5](=[O:12])[CH:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])[C:3]1=[O:23].N1C=CC=CC=1.[C:31](Cl)(=[O:35])[CH:32]([CH3:34])[CH3:33]>ClCCl>[CH3:1][C:2]1([CH3:24])[C:11]2[N:10]=[CH:9][CH:8]=[N:7][C:6]=2[C:5]([O:12][C:31](=[O:35])[CH:32]([CH3:34])[CH3:33])=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:19]([F:22])([F:21])[F:20])[C:3]1=[O:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62325Isobutyryl chlorideHCID 56968103HCID 56968103, compound

Product 1

HCID 69083478HCID 69083478, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of crude 8,8-dimethyl-6-(2-trifluoromethyl-phenyl)-8H-quinoxaline-5,7-dione (0.190 g) in dichloromethane (2.0 ml) at ambient temperature was added pyridine (0.054 g) followed by isobutryl chloride (isopropyl-C(O)—Cl, 0.064 g) and the reaction mixture stirred for 1 hour. The reaction mixture was concentrated and the residue purified by chromatography on silica gel (eluent 5-95% ethyl acetate in isohexane) to give isobutyric acid 8,8-dimethyl-7-oxo-6-(2-trifluoromethyl-phenyl)-7,8-dihydro-quinoxalin-5-yl ester (compound F1 of Table F) (0.162 g).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue purified by chromatography on silica gel (eluent 5-95% ethyl acetate in isohexane)

Sources & evidence

ORD record
ord-77b842f05a224e9fbf43e614382c938f
Source dataset
uspto-grants-2015_02
Patent number
US08962628B2

Reaction notes

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