Triphenylphosphine → HCID 10024407, compound

Participants

Reaction Conditions

Reaction Steps

To 2-(8-fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol (0.21 g, 1.10 mmol), 2-(6-chloro-3-fluoropyridin-2-yl)-5-fluorobenzonitrile (0.25 g, 1.00 mmol) and palladium acetate (0.011 g, 0.05 mmol) in N,N-dimethylacetamide (2 ml) was added triphenylphosphine (0.013 g, 0.05 mmol) followed by potassium acetate (0.14 g, 1.51 mmol) and the mixture heated at 130° C. for 2 h. The reaction was cooled to ambient temperature, diluted with methanol (8 ml) and 2 drops of acetic acid were added. The mixture was poured onto a strong cation exchange cartridge and eluted with several column lengths of methanol. Several column lengths of 2N ammonia in methanol were then eluted to recover the product. The pale yellow oil was chromatographed on silica, eluting with 3% methanol in dichloromethane, to give the title material as a white powdery solid. Recrystallised from ethyl acetate/ether to afford the title compound (215 mg): δH (400 MHz, CDCl3) 1.73 (6H, s), 2.07 (1H, s), 7.26 (1H, d, J 14.4), 7.45-7.49 (1H, m), 7.61 (1H, dd, J 2.6, 7.9), 7.67 (1H, t, J 9.0), 7.77-7.80 (1H, m), 7.88 (1H, dd, J 3.3, 8.9), 8.15 (1H, s), 9.59 (1H, d, J 7.3); m/z (ES+) 409.

Provenance & Evidence