3-(Ethylsulfonamido)phenylboronic acid → Ethanesulfonic acid [3-(2-methoxy-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-amide

HRID 2218684Notes

Reaction equation

HRID 2218684 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.[CH2:20]([S:22]([NH:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)(=[O:24])=[O:23])[CH3:21]>>[CH3:15][O:14][C:12]1[CH:11]=[CH:10][C:9]2[C:3](=[CH:2][C:28]3[CH:27]=[C:26]([NH:25][S:22]([CH2:20][CH3:21])(=[O:24])=[O:23])[CH:31]=[CH:30][CH:29]=3)[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 467388243-(Ethylsulfonamido)phenylboronic acidHCID 689347185-bromomethylene-2-methoxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 70996758Ethanesulfonic acid [3-(2-methoxy-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-amide

Procedure

Following the procedures essentially as described in Example 219, below, and using 5-bromomethylene-2-methoxy-10,11dihydro-5H-dibenzo[a,d]cycloheptene (E/Z mixture, 97 mg, 0.31 mmol) with 3-ethanesulfonylaminophenylboronic acid (78 mg, 0.34 mmol) to give 57 mg (44%) of an E/Z mixture of the title compound. MS (ES) 420 (M+1) weak, 418 (M−1). HPLC shows 45% of the E isomer and 53% of the Z isomer.

Sources & evidence

ORD record
ord-d528e25f23ac465db0ded5aff663133f
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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