Diisobutylaluminum hydride → (1-methyl-1H-indazol-3-yl)methanol

To a stirring solution of 440 mg (2.31 mmol) of 1-Methyl-1H-indazole-3-carboxylic acid methyl ester (Fludzinski, P. et. al. J. Med. Chem. 1987, 30, 1535) in 10 mL dichloromethane at -78° C. is added dropwise over 5 min a solution of 5.8 mL (5.8 mmol, 2.5 equiv) of a 1.0M solution of DIBAL-H in hexane. The resulting solution is allowed to slowly warm to RT over a 3 h period then quenched by careful addition of 5 mL of H2O. The reaction mixture is poured into 100 mL of EtOAc and extracted with 1N HCl (1×100 mL), dried (MgSO4), and the solvent removed in vacuo. Purification of the crude material by silica gel flash column chromatography using hexane/EtOAc 1/1 as eluent afforded 340 mg of the title compound as a pale yellow oil: 1H NMR (CDCl3, 300 MHz) δ7.80 (d, 1H), 7.42-7.12 (m, 3H), 5.02 (d, 2H), 4.00 (s, 3H), 2.27 (m, 1H); Rf =0.25 in hexane/EtOAc 1/1.

1. customthen quenched by careful addition of 5 mL of H2O
2. additionThe reaction mixture is poured into 100 mL of EtOAc
3. extractionextracted with 1N HCl (1×100 mL)
4. dry with materialdried (MgSO4)
5. customthe solvent removed in vacuo
6. customPurification of the crude material by silica gel flash column chromatography

ORD record

ord-ac953208cf3144fca98e034a61833c8f

Source dataset

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05859007