2-(1,3-Dioxolan-2-yl)-5-fluoro-3-nitropyridine → 2-(1,3-Dioxolan-2-yl)-5-fluoropyridin-3-amine

HRID 473425Notes

Reaction equation

[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]([F:15])=[CH:8][N:7]=1>C(O)C.[Pd]>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[C:11]([NH2:12])=[CH:10][C:9]([F:15])=[CH:8][N:7]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 2-(1,3-dioxolan-2-yl)-5-fluoro-3-nitropyridine (10 g, 46.69 mmol) in ethanol (140 mL) was added Pd/C (1 g) under nitrogen atmosphere. The reaction mixture was stirred for overnight under hydrogen atmosphere at 25° C. The reaction mixture was filtered through Celite™ and washed with EtOH. The filtrate was concentrated in vacuo and residue was purified by column chromatography on silica gel using 0-40% EtOAc in hexane to give 2-(1,3-dioxolan-2-yl)-5-fluoropyridin-3-amine: LC-MS (ESI) m/z 185.2 [M+H]+.

Workup

filtrationThe reaction mixture was filtered through Celite™
washwashed with EtOH
concentrationThe filtrate was concentrated in vacuo and residue
customwas purified by column chromatography on silica gel using 0-40% EtOAc in hexane

Sources & evidence

ORD record: ord-240e2ea14cb44ba8968023eae600c48d
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633313B2

Reaction notes

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