Pyridine → HCID 67087558, compound

HRID 57191Notes

Reaction equation

N1C=CC=CC=1.[CH2:7]([O:9][C:10]1[C:15]([C:16]2(O)[C:24]3[C:19](=[CH:20][C:21]([F:27])=[C:22]([C:25]#[N:26])[CH:23]=3)[NH:18][C:17]2=[O:28])=[CH:14][CH:13]=[CH:12][N:11]=1)[CH3:8].S(Cl)([Cl:32])=O>ClCCl>[Cl:32][C:16]1([C:15]2[C:10]([O:9][CH2:7][CH3:8])=[N:11][CH:12]=[CH:13][CH:14]=2)[C:24]2[C:19](=[CH:20][C:21]([F:27])=[C:22]([C:25]#[N:26])[CH:23]=2)[NH:18][C:17]1=[O:28]

Participants

Conditions

Temperature: 0 °C

Procedure

0.47 ml (5.81 mmol) of pyridine was added to 1.3 g (4.15 mmol) of 3-(2-ethoxypyridin-3-yl)-6-fluoro-3-hydroxy-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile in 30 ml of dichloromethane. After the reaction mixture had been cooled to 0° C., 0.42 ml (5.81 mmol) of thionyl chloride was added dropwise. The mixture was stirred at room temperature for one hour and then poured into ice-water. After stirring for 15 minutes, the organic phase was separated off. The aqueous phase was extracted several times with dichloromethane. The combined organic phase was dried over magnesium sulfate and filtered, and the solvent was removed in vacuo. 1.13 g of 3-chloro-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile were obtained as a solid which was employed without further purification in the next stage.

Workup

stirringAfter stirring for 15 minutes
customthe organic phase was separated off
extractionThe aqueous phase was extracted several times with dichloromethane
dry with materialThe combined organic phase was dried over magnesium sulfate
filtrationfiltered
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-d4e52df6dda344368bd720a15fafb1cf
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434713B2

Reaction notes

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