3-Methylsulfonylaminophenylboronic acid → N-[3-(1,9-Difluoro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-methanesulfonamide

HRID 2218698Notes

Reaction equation

HRID 2218698 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8](B(O)O)[CH:9]=[CH:10][CH:11]=1)(=[O:4])=[O:3].Br[CH:16]=[C:17]1[C:23]2[CH:24]=[CH:25][CH:26]=[C:27]([F:28])[C:22]=2[CH2:21][CH2:20][C:19]2[C:29]([F:33])=[CH:30][CH:31]=[CH:32][C:18]1=2>>[F:28][C:27]1[C:22]2[CH2:21][CH2:20][C:19]3[C:29]([F:33])=[CH:30][CH:31]=[CH:32][C:18]=3[C:17](=[CH:16][C:8]3[CH:7]=[C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:11]=[CH:10][CH:9]=3)[C:23]=2[CH:24]=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 27735353-Methylsulfonylaminophenylboronic acidHCID 689374405-bromomethylene-1,9-difluoro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 59769949N-[3-(1,9-Difluoro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-methanesulfonamideYield 134.3%

Procedure

Following procedures essentially as described in Example 219, below, and using 3-methanesulfonamidophenyl boronic acid (592 mg, 2.75 mmol) and 5-bromomethylene-1,9-difluoro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (803 mg, 2.75 mmol), provides 1.52 g of the title compound crude product. The crude product is purified using column chromatography (15% EtOAc/hexane to 30% EtOAc/hexane) to give 690 mg (67%) white solid. MS (ES) 410 (M−1). HPLC (ISO90-10M) shows 92% purity at t=2.64 min.

Sources & evidence

ORD record
ord-deab9f00e4cf45ccaf8b0876ae1bbec2
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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