Aluminium lithium hydride → (5-Fluoro-1H-pyrrolo[2,3-b]pyridin-4-yl)methanol

Temperature

0 °C

To an oven-dried 200 mL round bottom flask equipped for stirring was added methyl 5-fluoro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate (2.4 g, 12.36 mmol) under nitrogen. THF (100 mL) was added and the colorless solution was cooled to 0° C. Lithium aluminum hydride (27.2 mL, 27.2 mmol) was added and the solution was stirred at 0° C. for 3 h. The reaction was quenched with EtOAc (100 mL); brine (100 mL) was added, and the aqueous phase was extracted three times with EtOAc. The organics were dried over Na2SO4 and concentrated to afford the title compound as a yellow fine powder (2.01 g, 98%). 1H NMR (400 MHz, CD3OD) δ 4.96 (d, J=1.26 Hz, 2 H) 6.72 (d, J=3.54 Hz, 1 H) 7.44 (d, J=3.54 Hz, 1 H) 8.06 (d, J=2.78 Hz, 1 H). [M+H] calc'd for C8H7FN2O, 167; found, 167.5.

1. customTo an oven-dried 200 mL round bottom flask equipped
2. stirringthe solution was stirred at 0° C. for 3 h
3. customThe reaction was quenched with EtOAc (100 mL)
4. additionbrine (100 mL) was added
5. extractionthe aqueous phase was extracted three times with EtOAc
6. dry with materialThe organics were dried over Na2SO4
7. concentrationconcentrated

ORD record

ord-7d886432170f4283a84e34bc4ed30aa6

Source dataset

uspto-grants-2013_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08420816B2