Triethylsilane → HCID 58558117, compound

Participants

Reaction Steps

A solution of benzyl 4-(3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazin-8-yl)piperidine-1-carboxylate (0.580 g, 1.15 mmol, prepared using R from 1-(benzyloxycarbonyl)piperidine-4-carboxylic acid (Matrix), S from Example #3 Step E, E with TFA, KKKK with PFPAA, D with NaOH, KK), TEA (0.03 mL, 0.229 mmol), palladium (II) chloride (0.020 g, 0.115 mmol) in triethylsilane (18.3 mL, 115 mmol) was heated at about 120° C. for about 8 h. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The product was purified by silica gel chromatography eluting with a gradient of 0-10% (90:9:1) (MeOH/DCM/DEA) in DCM to give 8-(piperidin-4-yl)-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[1,2-a]pyrrolo[2,3-e]pyrazine (0.234 g, 55%) as a brown oil: LC/MS (Table 1, Method b) Rt=1.93 min; MS m/z: 372 (M+H)+.

Provenance & Evidence