Bromoacetyl bromide → HCID 10272492, compound

Participants

Reaction Steps

(Chart E, Step 1): A dry round bottom flask is charged with AlCl3 (66.7 mg, 0.5 mmol) and dichloromethane (4 mL) to make a heterogeneous solution. Dropwise addition of bromo-acetylbromide (0.044 mL, 0.5 mmol) turns the reaction into a homogeneous orange solution. After 30 minutes of stirring at ambient temperature, a solution of 2,2,2-trifluoro-1-(1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indol-3-yl)-1-ethanone (141.1 mg, 0.5 mmol) in dichloromethane (2 mL) is added dropwise and stirred for three days. The reaction turns dark purple within the first 4 hours of stirring. The reaction is poured in a sat. aq. NaHCO3 solution and extracted three times with dichloromethane. The combined organics are combined, dried with MgSO4, filtered and concentrated to 192 mg of a purple foam. The crude is purified by LC (230-400 silica gel) eluting with 10% ethyl acetate and 20% dichloromethane in heptane to afford 120 mg of 1-[11-(2-bromoacetyl)-1,2,4,5-tetrahydro-3H-[1,4]diazepino[1,7-a]indol-3-yl]-2,2,2-trifluoro-1-ethanone as a white foam.

Provenance & Evidence