Potassium Carbonate → HCID 59654674, compound

HRID 2053110Notes

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-b8447ead75df46f4954489c2eff9e338
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07326732B2

Reaction notes

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