Chlorotrimethylsilane → HCID 58529613, compound

Participants

Reaction Conditions

Reaction Steps

Chlorotrimethylsilane (89 mL, 0.70 mol) was added drop wise to a stirred solution of 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine in tetrahydrofuran (1.6 L, anhydrous) and stirring was continued for 3 h. The solution was cooled to 0° C. and 2-propyl magnesium chloride solution (2M in THF, 740 mL, 1.48 mol) was slowly added. The reaction was warmed to 25° C. and stirring continued for 2 h, then cooled back down to −5° C. and a solution of N-tert-butoxycarbonyl piperidine (91.0 g, 0.68 mol) in THF (1 L) was added drop wise. The reaction was continued for 18 h at 25° C., then the mixture was, poured into vigorously-stirred ice water (8 L). The aqueous mixture was extracted with ethyl acetate (3×3 L) and the combined organic portions were dried over magnesium sulfate. Filtration and concentration in vacuo gave a dark-orange oil which was dissolved in a minimal volume of dichloromethane and crystallization induced. After cooling (−10° C.) the mixture for several hours, the crystalline product was collected by suction filtration, washed with diethyl ether and dried to give a colorless solid (61 g, 52%). Purification of the filtrate by silica gel chromatography (5% methanol/dichloromethane) yielded additional product (37 g, 32%). 1H-NMR (DMSO-d6) δ 7.77 (s, 1H), 7.69 (br s, 2H), 6.80 (d, 1H), 6.55 (d, 1H), 5.74 (s, 1H), 3.77 (m, 2H), 3.15 (br m, 2H), 2.48 (m, 2H), 1.70 (d, 2H), 1.40 (s, 9H). ES-MS m/z=334.1 [M+H]+, RT (min) 2.15.

Provenance & Evidence