Methyl iodide → 7-Bromo-2-methyl-1,6-naphthyridine

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[N:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11](=O)[CH3:12].C[S-].[Na+].IC>C(O)C>[Br:8][C:6]1[CH:7]=[C:2]2[C:3]([CH:9]=[CH:10][C:11]([CH3:12])=[N:1]2)=[CH:4][N:5]=1

Participants

Procedure

(E)-4-(4-Amino-6-bromopyridin-3-yl)but-3-en-2-one (Preparation 66, 331 mg 1.37 mmol) and sodium thiomethoxide (97.5 mg 1.39 mmol) were stirred in ethanol (2.9 mL) at 20° C. for 50 minutes. Iodomethane (86 uL, 1.38 mmole) was added and the reaction stirred for another 45 minutes. The reaction was concentrated in vacuo and diluted with ethyl acetate (30 mL) and washed with water (10 mL). The aqueous was back extracted with ethyl acetate (5 mL) and the combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo to afford the title compound (275 mg, 89%).