5-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene → 5-(10,11-Dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-2-methyl-phenylamine

Participants

Reaction Steps

Following the procedure essentially as described for Example 219, below, and using 5-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (300 mg, 1.05 mmol) and (3-amino-4-methylphenyl)boronic acid hydrochloride (217 mg, 1.16 mmol), yields 245 mg (75%) 5-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-2-methyl-phenylamine as a brown oil. Then, following procedures essentially as described in Example 90, below, and using 5-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-2-methyl-phenylamine (100 mg, 0.321 mmol), affords 35 mg (28%) of the title compound as a colorless oil. MS (ES) 407 (M+NH4), 388 (M−H); HPLC shows 98% purity.

Provenance & Evidence