Water → HCID 21833055, compound

HRID 582505Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][C:4]([C:7]([C:9]2[O:10][C:11]3[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14](Br)[C:12]=3[CH:13]=2)=[O:8])=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[O:47]1[CH2:51]CCC1.[OH2:52]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:19][O:18][C:17]1[CH:16]=[CH:15][C:14]([C:51]([OH:47])=[O:52])=[C:12]2[C:11]=1[O:10][C:9]([C:7]([C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)=[O:8])=[CH:13]2

Participants

Conditions

Temperature: 80 °C

Procedure

2-[(Pyridin-4-yl)carbonyl]-4-bromo-7-methoxybenzofuran (3.3 g), triphenylphosphine (1 g), bis(triphenylphosphine)palladium (II) chloride (0.47 g), triethylamine (14 ml), tetrahydrofuran (150 ml) and H2O (57 ml) were combined in a Parr pressure reactor. The vessel was purged with carbon monoxide, charge to 180 psi with carbon monoxide and then heated to 80° C. with stirring for 3 days. On cooling and release of pressure the tetrahydrofuran was removed in vacuo. The remaining aqueous mixture was basified to pH14 with 1N sodium hydroxide solution (250 ml) and washed with ethyl acetate (200 ml). The aqueous layer was then acidified to pH5 with acidic acid under ice bath cooling. The resulting precipitate was collected by filtration and dried to give a beige solid (2.97 g). M.S. M+H observed

Workup

customThe vessel was purged with carbon monoxide
additioncharge to 180 psi with carbon monoxide
temperatureOn cooling
customrelease of pressure the tetrahydrofuran was removed in vacuo
washwashed with ethyl acetate (200 ml)
temperaturecooling
filtrationThe resulting precipitate was collected by filtration
customdried

Sources & evidence

ORD record: ord-716fb5dd4a324c07947736b9fdc180c8
Source dataset: uspto-grants-1999_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05925636

Reaction notes

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