Potassium Acetate → HCID 22126044, compound

HRID 1858176Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:28])=[C:24](I)[CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:30]1[S:31][C:32]([Cl:35])=[CH:33][CH:34]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:36]([O-:39])(=[O:38])C.[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:28])=[C:24]([C:36]([OH:39])=[O:38])[CH:25]=2)[NH:20][C:19](=[O:29])[C:18]=1[C:30]1[S:31][C:32]([Cl:35])=[CH:33][CH:34]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-{2-[7-chloro-3-(5-chlorothiophen-2-yl)-6-iodo-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (612 mg in 15 ml methylsulfoxide) was added 34 mg [1,1'-bis(diphenylphosphino)ferrocene)dichloropalladium (II) followed by 410 mg potassium acetate and the mixture heated to 60° C. under an atmosphere of carbon monoxide. After 5.5 hours, the mixture was cooled to room temperature and partitioned between ethyl acetate and 0.5N hydrochloric acid and extracted. The organic portion was dried over sodium sulfate and the concentrate purified by flash chromatography on silica gel (ethyl acetate:hexane, 20:80; then 30:70; then 40:60; then 50:50) to give the title compound (337 mg).

Workup

temperaturethe mixture was cooled to room temperature
custompartitioned between ethyl acetate and 0.5N hydrochloric acid
extractionextracted
dry with materialThe organic portion was dried over sodium sulfate
customthe concentrate purified by flash chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record: ord-9b1baccfd5d3433a94b344efdf844a54
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150522

Reaction notes

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