5-bromomethylene-10,11-dihydro-5H-dibenzo[a,d]cycloheptene → HCID 59769895, compound

HRID 2218627Notes

Reaction equation

HRID 2218627 reaction equation
[CH3:1][C:2]1[C:7](B2OC(C)(C)C(C)(C)O2)=[CH:6][CH:5]=[CH:4][C:3]=1[NH:17][S:18]([CH3:21])(=[O:20])=[O:19].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:7]3[C:2]([CH3:1])=[C:3]([NH:17][S:18]([CH3:21])(=[O:19])=[O:20])[CH:4]=[CH:5][CH:6]=3)[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 58613440N-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanesulfonamide

Product 1

HCID 59769895HCID 59769895, compoundYield 13.2%

Procedure

Following the procedures essentially as described in Example 219, below, and using N-[2-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), purification by UV-guided semi-preparatory reverse-phase HPLC affords 18 mg (13%) of the title compound as a yellow oil. MS (ES) 407 M+NH4), 388 (M−H); HPLC shows 96% purity.

Sources & evidence

ORD record
ord-0ef03af8d4414d6a8244f0a33dbcaed7
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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