Sodium borohydride → Imidazo[1,2-b]pyridazin-6-ylmethanol

Reaction equation

[BH4-].[Na+].[N:3]1[CH:4]=[CH:5][N:6]2[C:11]=1[CH:10]=[CH:9][C:8]([C:12](OC)=[O:13])=[N:7]2>C1COCC1.CO>[N:3]1[CH:4]=[CH:5][N:6]2[C:11]=1[CH:10]=[CH:9][C:8]([CH2:12][OH:13])=[N:7]2

Participants

Procedure

Sodium borohydride (1.1 g, 31.1 mmol) was added to a solution of methyl imidazo[1,2-b]pyridazine-6-carboxylate (2.4 g, 15.5 mmol) in THF (35 mL) and methanol (2.5 ml) at RT. The reaction mixture was stirred at RT for 2 h (the reaction was monitored by TLC) upon which the mixture was concentrated under reduced pressure. The reaction mixture was diluted with water and extracted with EtOAc. The combined organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford imidazo[1,2-b]pyridazin-6-ylmethanol (1.6 g, 81%) as a white solid. 1H NMR: 200 MHz, DMSO-d6: δ 8.5 (s, 1H), 8.3 (d, 1H), 7.9 (s, 1H), 7.55 (d, 1H), 5.65 (t, 1H), 4.6 (d, 2H). MS: [M+H]+: m/z=311.2.