Water → (3E)-3-{5,5-dimethyl-4-[6-(2-morpholin-4-ylethyl)pyridin-3-yl]furan-2(5H)-ylidene}-6-fluoro-1,3-dihydro-2H-indol-2-one

HRID 333388Notes

Reaction equation

[CH3:1][C:2]1([CH3:26])[O:6]/[C:5](=[C:7]2/[C:8](=[O:17])[NH:9][C:10]3[C:15]/2=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=3)/[CH:4]=[C:3]1[C:18]1[CH:19]=[N:20][C:21]([CH:24]=[CH2:25])=[CH:22][CH:23]=1.[NH:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1.O>CN(C=O)C>[CH3:1][C:2]1([CH3:26])[O:6]/[C:5](=[C:7]2/[C:8](=[O:17])[NH:9][C:10]3[C:15]/2=[CH:14][CH:13]=[C:12]([F:16])[CH:11]=3)/[CH:4]=[C:3]1[C:18]1[CH:19]=[N:20][C:21]([CH2:24][CH2:25][N:27]2[CH2:32][CH2:31][O:30][CH2:29][CH2:28]2)=[CH:22][CH:23]=1

Participants

Conditions

Temperature: 96 °C

Procedure

A mixture of (3E)-3-[5,5-dimethyl-4-(6-vinylpyridin-3-yl)furan-2(5H)-ylidene]-6-fluoro-1,3-dihydro-2H-indol-2-one (50 mg, 0.14 mmol) and morpholine (0.2 mL, 2.3 mmol) in 5 mL of DMF was heated in 96° C. bath under nitrogen for 3 hours. The mixture was cooled to room temperature and poured into 100 mL of water. The precipitates were filtered, washed with water and dried in vacuo to give (3E)-3-{5,5-dimethyl-4-[6-(2-morpholin-4-ylethyl)pyridin-3-yl]furan-2(5H)-ylidene}-6-fluoro-1,3-dihydro-2H-indol-2-one as a brown solid. Yield: 40 mg, 64%.

Workup

temperatureThe mixture was cooled to room temperature
filtrationThe precipitates were filtered
washwashed with water
customdried in vacuo

Sources & evidence

ORD record: ord-75c8f9fe04764a6cb3ba7200b46b3fc2
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877923B2

Reaction notes

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