Diisobutylaluminum hydride → (1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)methanol

A solution of methyl 1-(4-fluorophenyl)-6-methyl-1H-indazole-5-carboxylate (1.52 g, 5.35 mmol) and THF (36 mL) was cooled to about 0° C. and to it was added DIBAL-H (1 M solution in toluene, 11.2 mL, 11.2 mmol) and stirred for about 2 h. To the reaction mixture was added DIBAL-H (1 M solution in toluene, 6.0 mL, 6.0 mmol) and stirring was continued for 2 h. The reaction was quenched with EtOAc (˜20 mL) and allowed to warm to ambient temperature. To the reaction mixture was added 10% aqueous Rochelle's salt (40 mL) and stirred for about 16 h. The reaction mixture was partially concentrated under reduced pressure and partitioned between EtOAc (60 mL) and water (20 mL). The aqueous layer was back extracted with EtOAc (30 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, DCM/MeOH 100:0 to 0:10) to afford (1-(4-fluorophenyl)-6-methyl-1H-indazol-5-yl)methanol (1.14 g, 4.45 mmol, 83%). LC-MS (Table 1, Method g) Rt=2.01 min, m/z 257 (M+H)+.

1. stirringstirring
2. waitwas continued for 2 h
3. customThe reaction was quenched with EtOAc (˜20 mL)
4. additionTo the reaction mixture was added 10% aqueous Rochelle's salt (40 mL)
5. stirringstirred for about 16 h
6. concentrationThe reaction mixture was partially concentrated under reduced pressure
7. custompartitioned between EtOAc (60 mL) and water (20 mL)
8. extractionThe aqueous layer was back extracted with EtOAc (30 mL)
9. dry with materialThe combined organic layers were dried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. customThe residue was purified by column chromatography (SiO2, DCM/MeOH 100:0 to 0:10)

ORD record

ord-095d9aa457af4df5962a5199d51a17e1

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150592B2