2-Fluoropyridine → 6-chloro-N-2-pyridinyl-3-pyridinemethanamine

HRID 1474062Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Cl:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][NH2:16])=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>CN1CCCC1=O>[Cl:8][C:9]1[N:14]=[CH:13][C:12]([CH2:15][NH:16][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 230 °C

Procedure

A mixture of 2-fluoropyridine (1.4 g, 15 mmol) and 6-chloro-3-pyridinemethanamine (alternatively named 5-aminomethyl-2-chloropyridine) (2.55 g, 18 mmol) in N-methylpyrrolidinone (5 mL) was heated at 230° C. in a microwave reactor for 30 min. This reaction was repeated four times using the same amounts of starting materials for each repetition. All five of the reaction mixtures were then poured into saturated aqueous sodium bicarbonate solution and extracted into ethyl acetate. The organic layer was washed with saturated aqueous sodium bicarbonate solution, dried over Na2SO4, and concentrated under reduced pressure. The crude product was then purified by chromatography on silica gel using 10% ethyl acetate in hexanes as the eluent to provide the title compound as an oil (5.1 g).

Workup

customAll five of the reaction mixtures
extractionextracted into ethyl acetate
washThe organic layer was washed with saturated aqueous sodium bicarbonate solution
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customThe crude product was then purified by chromatography on silica gel using 10% ethyl acetate in hexanes as the eluent

Sources & evidence

ORD record: ord-fb6357a063f44f61b208d1e1ba05ec76
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018220B2

Reaction notes

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