Methanol → (5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methanol

Reaction equation

C([O:4][CH2:5][C:6]1[CH:7]=[C:8]([Br:23])[CH:9]=[C:10]2[C:14]=1[N:13]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:12]=[CH:11]2)(=O)C.CO.C(=O)([O-])[O-].[K+].[K+]>>[Br:23][C:8]1[CH:9]=[C:10]2[C:14](=[C:6]([CH2:5][OH:4])[CH:7]=1)[N:13]([CH2:15][O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])[N:12]=[CH:11]2

Participants

Reactant 3

HCID 887Methanol

HCID 11430Potassium Carbonate

HCID 57546198(5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methyl acetate

Product 1

HCID 57546160(5-Bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methanol

Procedure

To a solution of (5-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-7-yl)methyl acetate (1.04 g, 2.60 mmol) in methanol (15 mL, 371 mmol) at room temperature was added potassium carbonate (200 mg, 1.45 mmol). After 20 min, the reaction was concentrated and the resulting residue partitioned between water and diethyl ether. The ethereal was washed with water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (12%→25% EtOAc/Hex) gave 0.73 g (78%) as a colorless oil that solidified to an amorphous white solid upon standing. 1H-NMR (CDCl3, 500 MHz) δ 7.91 (s, 1H), 7.81 (d, J=1.5, 1H), 7.43 (d, J=1.8, 1H), 5.90 (s, 2H), 4.97 (d, J=6.4, 2H), 3.49 (m, 2H), 3.43 (t, J=6.4, 1H), 0.83 (m, 2H), −0.09 (s, 9H); 13C NMR(126 MHz, CDCl3) δ ppm 136.7, 133.5, 131.1, 128.1, 125.9, 123.6, 114.4, 80.0, 66.6, 62.5, 17.8, −1.4.