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

HRID 2218729Notes

Reaction equation

HRID 2218729 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH2:5][CH2:6][C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[C:9](=O)[C:10]=2[N:11]=1.[CH:17](Br)=[CH2:18].[OH:20][C:21]1[CH:22]=C(B(O)O)[CH:24]=[CH:25][CH:26]=1>>[CH3:1][C:2]1[O:3][C:4]2[CH2:5][CH2:6][C:7]3[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=3[C:9](=[CH:24][C:25]3[CH:26]=[C:21]([OH:20])[CH:22]=[CH:17][CH:18]=3)[C:10]=2[N:11]=1

Participants

4

Reactant 3

HCID 11641BromoetheneHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 122003742-Methyl-9,10-dihydro-benzo[5,6]cyclohepta[1,2-d]oxazol-4-one2×

Product 1

HCID 689350263-(2-Methyl-9,10-dihydro-1-oxa-3-aza-benzo[f]azulen-4-ylidenemethyl)-phenol

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-hydroxyphenyl boronic acid (207 mg, 1.5 mmmol). Purify the crude product using column chromatography (15% EtOAc/hexane to 30% EtOAc/hexane) to give 26 mg title compound, MS (ES) 304 (M+1). HPLC shows 93% purity at t=2.48 min.

Workup

  1. customPurify the crude product

Sources & evidence

ORD record
ord-d1beac0382e94efbbb63a4a0ab38495b
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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