Water → HCID 21833055, compound

HRID 1740756Notes

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>[N:1]1[CH:6]=[CH:5][C:4]([C:7]([C:9]2[O:10][C:11]3[C:12](=[C:14]([C:51]([OH:47])=[O:52])[CH:15]=[CH:16][C:17]=3[O:18][CH3:19])[CH:13]=2)=[O:8])=[CH:3][CH:2]=1

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 water (57 ml) were combined in a Parr pressure reactor. The vessel was purged with carbon monoxide, charged 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 acetic acid under ice bath cooling. The resulting precipitate was collected by filtration and dried to give a beige solid (2.97 g).

Workup

customThe vessel was purged with carbon monoxide
additioncharged 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-3625b0a02ae24fa7bc6f8ce46d88fb7b
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05972936

Reaction notes

Loading…