3-(Tributylstannyl)pyridine → HCID 54285809, compound

Participants

Reaction Steps

The 2-(1-BOC-2-(S)-pyrrolidinyl)-6-bromofuro[3,2-b]pyridine (0.24g, 0.64 mmol) obtained from Example 46a above was dissolved in toluene (6 mL). Tributyl-3-pyridyltin (0.36 g, 1.3 mmol), palladium (O) tetrakis(triphenyl phosphine) (40 mg) was then added to the toluene solution and the resultant mixture was heated under reflux for 16 h. The desired product was extracted with CH2Cl2, dried over MgSO4 and filtered. Solvent was then removed under reduced pressure and the residue was chromatographed (silica gel: Hexane/EtOAc, 5:1 to EtOAc) to afford an oil (0.13 g, 56%). MS (CI/NH3) m/z: 366 (M+H)+; 1H NMR (CDCl3, 300 MHz) δ 1.33, 1.55 (2s, 9H), 1.92-2.38 (m, 3H), 3.43-3.70 (m, 2H), 5.08 (m, 1H), 5.15 (m, 1H), 6.75 (brs, 1H), 7.43 (m, 1H), 7.86 (s, 1H), 7.93 (m, 1H), 8.66 (m, 1H), 8.72 (brs, 1H), 8.89 (s, 1H).

Provenance & Evidence