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

HRID 2218625Notes

Reaction equation

HRID 2218625 reaction equation
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]1=2.Cl.[NH2:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][C:25]=1[CH3:26]>>[CH:14]1[C:5]2[CH2:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=3[C:3](=[CH:2][C:22]3[CH:23]=[CH:24][C:25]([CH3:26])=[C:20]([NH2:19])[CH:21]=3)[C:4]=2[CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 52579405-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneHCID 16427087(3-Amino-4-methylphenyl)boronic acid--hydrogen chloride (1/1)

Product 1

HCID 689355975-(10,11-Dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-2-methyl-phenylamineYield 75%

Procedure

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.

Sources & evidence

ORD record
ord-c99bcf8fcfa744ad9a4ea572d1dbd08f
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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