Sodium borohydride → HCID 178515761, compound
Reaction equation
[OH:1][C:2]1[N:7]=[C:6]2[N:8]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]3=[O:17])[CH:9]=[N:10][C:5]2=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C>[OH:17][CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][CH:11]1[N:8]1[C:6]2=[N:7][C:2]([OH:1])=[CH:3][CH:4]=[C:5]2[N:10]=[CH:9]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
2-(5-Hydroxy-3H-imidazo[4,5-b]pyridin-3-yl)cyclohexanone (0.200 g, 0.865 mmol) was taken up in ethanol (4 mL) and sodium borohydride (9.8 mg, 0.26 mmol) added. The reaction was stirred at room temperature overnight. The solvent was removed under reduced pressure. The residue was purified by preparative HPLC to give the title compound (0.135 g). LCMS m/z=234.2 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.35-1.60 (m, 4H), 1.75-1.95 (m, 2H), 2.00-2.15 (m, 2H), 4.00-4.10 (m, 1H), 4.38 (q, J=8.1 Hz, 1H), 6.92 (d, J=8.8 Hz, 1H), 8.18 (d, J=8.8 Hz, 1H), 9.52 (s, 1H).