(4-Methanesulfonamidophenyl)boronic acid → N-[2-(2-Methoxy-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-methanesulfonamide

HRID 2218685Notes

Reaction equation

HRID 2218685 reaction equation
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][CH3:15])=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:16]=[CH:17][CH:18]=[CH:19][C:4]1=2.[CH3:20][S:21]([NH:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)(=[O:23])=[O:22]>>[CH3:15][O:14][C:12]1[CH:11]=[CH:10][C:9]2[C:3](=[CH:2][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=3[NH:24][S:21]([CH3:20])(=[O:23])=[O:22])[C:4]3[CH:19]=[CH:18][CH:17]=[CH:16][C:5]=3[CH2:6][CH2:7][C:8]=2[CH:13]=1

Participants

3

Reactant 2

HCID 2773537(4-Methanesulfonamidophenyl)boronic acidHCID 689347185-bromomethylene-2-methoxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 68937506N-[2-(2-Methoxy-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-methanesulfonamide

Procedure

Following the procedures essentially as described in Example 219, below, and using 5-bromomethylene-2-methoxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (E/Z mixture, 100 mg, 0.32 mmol) with 4-methanesulfonylaminophenylboronic acid (75 mg, 0.35 mmol) to give 35 mg (27%) of an E/Z mixture of the title compound. MS (ES) 406 (M+1), 404 (M−1). HPLC shows 53% of the E isomer and 44% of the Z isomer.

Sources & evidence

ORD record
ord-c56a9684e7b24b0c95b2312454a1c71c
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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