Potassium Carbonate → HCID 59654674, compound

HRID 1444206Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]([C:15]2[O:16][C:17](Br)=[CH:18][CH:19]=2)=[O:14])[CH:7]=1)[CH3:2].[CH3:22][N:23]([CH3:33])[C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.CC(O)=O.CC(O)=O.[Pd]>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]([C:15]2[O:16][C:17]([C:27]3[CH:28]=[CH:29][C:24]([N:23]([CH3:33])[CH3:22])=[CH:25][CH:26]=3)=[CH:18][CH:19]=2)=[O:14])[CH:7]=1)[CH3:2]

Participants

Conditions

Temperature: 70 °C

Procedure

To a previously degassed mixture of (3-[(5-bromo-furan-2-carbonyl)-amino]-phenyl)-acetic acid ethyl ester (11) (0.4 g), 4-(dimethylamino)phenylboronic acid (0.23 g), potassium carbonate (0.39 g) and tetra-n-butylammonium bromide (0.37 g) in water (2 ml) was added palladium II acetate (circa 10 mg). The mixture was heated to 70° C. for an hour, cooled and partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over sodium sulphate and evaporated in vacuo. Compound 13 (0.33 g) was obtained following silica gel column chromatography of the residue in 2:3 ethyl acetate:petroleum ether.

Workup

temperaturecooled
custompartitioned between ethyl acetate and water
customThe organic layer was separated
washwashed with brine
dry with materialdried over sodium sulphate
customevaporated in vacuo

Sources & evidence

ORD record: ord-8bd3bb677a1e42a4b3d827c2c2c82bf5
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07662839B2

Reaction notes

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