Bromoethene → n-[3-(2-Methyl-9,10-dihydro-1-oxa-3-aza-benzo[f]azulen-4-ylidenemethyl)-phenyl]-methanesulfonamide

HRID 2218728Notes

Reaction equation

[CH:1](Br)=[CH2:2].[CH3:4][C:5]1[O:6][C:7]2[CH2:8][CH2:9][C:10]3[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=3[C:12](=O)[C:13]=2[N:14]=1.[CH3:20][S:21]([NH:24][C:25]1[CH:26]=C(B(O)O)[CH:28]=[CH:29][CH:30]=1)(=[O:23])=[O:22]>>[CH3:4][C:5]1[O:6][C:7]2[CH2:8][CH2:9][C:10]3[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=3[C:12](=[CH:28][C:29]3[CH:30]=[C:25]([NH:24][S:21]([CH3:20])(=[O:23])=[O:22])[CH:26]=[CH:1][CH:2]=3)[C:13]=2[N:14]=1

Participants

Reactant 3

HCID 11641Bromoethene

HCID 27735353-Methylsulfonylaminophenylboronic acid

HCID 122003742-Methyl-9,10-dihydro-benzo[5,6]cyclohepta[1,2-d]oxazol-4-one

Product 1

HCID 68937112n-[3-(2-Methyl-9,10-dihydro-1-oxa-3-aza-benzo[f]azulen-4-ylidenemethyl)-phenyl]-methanesulfonamide

Procedure

Prepare the corresponding ketone (2-methyl-9,10-dihydro-1-oxa-3-aza-benzo[f]azulen-4-one) as described by E. E. Galantay, et al, J. Med. Chem. (17) 1316-1327 (1974) and convert to the corresponding Z-isomer of the vinyl bromide using procedures essentially as described in Preparations 23 and 24. Then, following procedures essentially as described in Example 219, combine the ketone with 3-methanesulfonamidophenyl boronic acid (325 mg, 1.5 mmmol). Purify the crude product using column chromatography (30% EtOAc/hexane to 50% EtOAc/hexane) to provide 180 mg (38%) Z-isomer as a light tan solid, mp 184.6° C., MS (ES) 381 (M+1), 379 (M−1). HPLC shows 94% purity at t=1.99 min.

Workup

customPurify the crude product
customto provide 180 mg (38%) Z-isomer as a light tan solid, mp 184.6° C., MS (ES) 381 (M+1), 379 (M−1)
customat t=1.99 min.

Sources & evidence

ORD record: ord-29856722fb6e40bba4e53e1271b91fc2
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07411072B2

Reaction notes

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