5-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene → N-[3-(10,11-Dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-4-methyl-phenyl]-methanesulfonamide

HRID 2218626Notes

Reaction equation

HRID 2218626 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH3:12])(=[O:11])=[O:10])=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.Br[CH:23]=[C:24]1[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=2[CH2:28][CH2:27][C:26]2[CH:35]=[CH:36][CH:37]=[CH:38][C:25]1=2>>[CH:35]1[C:26]2[CH2:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[C:24](=[CH:23][C:3]3[CH:4]=[C:5]([NH:8][S:9]([CH3:12])(=[O:10])=[O:11])[CH:6]=[CH:7][C:2]=3[CH3:1])[C:25]=2[CH:38]=[CH:37][CH:36]=1

Participants

3

Reactant 2

HCID 52579405-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cyclohepteneHCID 59770368N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanesulfonamide

Product 1

HCID 59770083N-[3-(10,11-Dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-4-methyl-phenyl]-methanesulfonamideYield 61%

Procedure

Following the procedures essentially as described in Example 219, below, and using N-[4-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanesulfonamide (120 mg, 0.386 mmol) and 5-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (100 mg, 0.351 mmol) affords 83 mg (61%) of the title compound as a yellow solid. MS (ES) 407 (M+NH4), 388 (M−H); HPLC shows 91% purity.

Sources & evidence

ORD record
ord-d3c6ef09856d4ef7ad43add0dac71fcf
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

Loading…