3-Methylsulfonylaminophenylboronic acid → N-[3-(2-Chloro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-methanesulfonamide

HRID 2218702Notes

Reaction equation

HRID 2218702 reaction equation
Br[CH:2]=[C:3]1[C:9]2[CH:10]=[CH:11][C:12]([Cl:14])=[CH:13][C:8]=2[CH2:7][CH2:6][C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]1=2.[CH3:19][S:20]([NH:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1)(=[O:22])=[O:21]>>[Cl:14][C:12]1[CH:11]=[CH:10][C:9]2[C:3](=[CH:2][C:26]3[CH:25]=[C:24]([NH:23][S:20]([CH3:19])(=[O:22])=[O:21])[CH:29]=[CH:28][CH:27]=3)[C:4]3[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=3[CH2:6][CH2:7][C:8]=2[CH:13]=1

Participants

3

Reactant 2

HCID 27735353-Methylsulfonylaminophenylboronic acidHCID 688868195-bromomethylene-2-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Product 1

HCID 68939254N-[3-(2-Chloro-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-methanesulfonamide

Procedure

Following procedures essentially as described in Example 219, below, and using 5-bromomethylene-2-chloro-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (100 mg, 0.313 mmol) and 3-methanesulfonylaminophenylboronic acid (74 mg, 0.344 mmol), affords 37 mg (29%) of the Z-isomer (Example 206(a)) of the title compound as a colorless oil (MS (ES) 408 (M−H). HPLC shows 99% purity. Continue to elute and obtain 23 mg (18%) of the E-isomer (Example (b)) of the title compound as a colorless oil (MS (ES) 408 (M−H); HPLC shows 92% purity).

Sources & evidence

ORD record
ord-ce0e240d972348efbcdef087b9d233f4
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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