Diisobutylaluminum hydride → (4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol

Temperature

-78 °C

To a solution of ethyl 4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (1.71 g, 3.88 mmol) in toluene (43.1 mL) at about −78° C. was added DIBAL-H (1 M in hexanes, 6.60 mL, 6.60 mmol) dropwise. The reaction was stirred for about 1 h at about −78° C. and the reaction mixture was warmed to ambient temperature and stirred for about 1 h. The reaction was quenched with saturated aqueous potassium sodium tartrate (15 mL) and the mixture was stirred for about 1 h. EtOAc (25 mL) was added and the layers were separated. The organic layer was dried over anhydrous Na2SO4, filtered through a pad of silica gel while washing with EtOAc (20 mL), and the filtrate was concd under reduced pressure. The residue was purified by silica gel chromatography eluting with a gradient of 0-50% EtOAc in DCM to give (4-(cyclohexylamino)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol (1.24 g, 80%) as an off white solid: LC/MS (Table 1, Method b) Rt=2.51 min; MS m/z: 400 (M+H)+.

1. temperaturethe reaction mixture was warmed to ambient temperature
2. stirringstirred for about 1 h
3. customThe reaction was quenched with saturated aqueous potassium sodium tartrate (15 mL)
4. stirringthe mixture was stirred for about 1 h
5. additionEtOAc (25 mL) was added
6. customthe layers were separated
7. dry with materialThe organic layer was dried over anhydrous Na2SO4
8. filtrationfiltered through a pad of silica gel
9. washwhile washing with EtOAc (20 mL)
10. customThe residue was purified by silica gel chromatography
11. washeluting with a gradient of 0-50% EtOAc in DCM

ORD record

ord-51a46eb5a9ec4a44b1f74dde8953d712

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08426411B2