Sodium Methoxide → 5-(4-(2,3-Di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)butyl)-3-methoxy-4,5-dihydroisoxazole
Reaction equation
Br[C:2]1[CH2:6][CH:5]([CH2:7][CH2:8][CH2:9][CH2:10][N:11]2[C:16]3=[N:17][C:18]([C:28]4[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=4)=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=4)[N:20]=[C:15]3[CH2:14][CH2:13][CH2:12]2)[O:4][N:3]=1.[CH3:35][O-:36].[Na+]>CO>[C:24]1([CH3:27])[CH:25]=[CH:26][C:21]([C:19]2[N:20]=[C:15]3[CH2:14][CH2:13][CH2:12][N:11]([CH2:10][CH2:9][CH2:8][CH2:7][CH:5]4[O:4][N:3]=[C:2]([O:36][CH3:35])[CH2:6]4)[C:16]3=[N:17][C:18]=2[C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)=[CH:22][CH:23]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 3-bromo-5-(4-(2,3-di-p-tolyl-7,8-dihydropyrido[2,3-b]pyrazin-5(6H)-yl)butyl)-4,5-dihydroisoxazole (step 1) (5195 mg, 10 mmol) in MeOH (5 ml) was treated with NaOMe (10 ml of 30% solution by weight) and heated at reflux for 2 hours. After cooling to RT, the reaction was quenched with water (100 ml) and the aqueous portion was extracted with EtOAc. The combined organic extracts were washed with brine, dried by passing through a phase separator and were concentrated under reduced pressure. The crude product was purified by chromatography on silica eluting with 0-60% EtOAc in iso-hexane to afford the titled compound as an orange oil;