Cesium carbonate → HCID 24987662, compound

HRID 1097845Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][CH:16]([N:19]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH2:21][C:20]4=[O:28])[CH2:15][CH2:14]3)=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.Cl.Cl[CH2:31][CH2:32][N:33]([CH3:35])[CH3:34].C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.[OH-].[Na+]>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([N:13]3[CH2:18][CH2:17][CH:16]([N:19]4[C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[CH2:21][C:20]4=[O:28])[CH2:15][CH2:14]3)=[O:12])=[CH:7][N:8]2[CH2:31][CH2:32][N:33]([CH3:35])[CH3:34])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A suspension of 0.40 g (1.0 mmol) 1-[1-(6-chloro-1H-indole-3-carbonyl)-piperidin-4-yl]-1,3-dihydro-indol-2-one, 0.16 g (1.1 mmol) 1-chloro-2-dimethylaminoethane hydrochloride and 0.69 g (2.1 mmol) cesium carbonate in 10 ml acetonitrile was heated at 50° C. over night. After cooling to room temperature the reaction mixture was diluted with a 0.5 M aqueous solution of sodium hydroxide and extracted with three portions of ethyl acetate. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo. Flash chromatography gave 0.18 g (39%) of the title compound.

Workup

temperatureAfter cooling to room temperature the reaction mixture
extractionextracted with three portions of ethyl acetate
washThe combined organic extracts were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6a2da020dac941b79c1bf6e938d7490c
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08143281B2

Reaction notes

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