Potassium Carbonate → HCID 18797470, compound

HRID 1457000Notes

Reaction equation

[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]3[CH2:12][CH2:13][NH:14][CH2:15][CH:16]=3)=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][C:24](=[O:27])[CH2:25]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][C:24](=[O:27])[CH2:25][N:14]1[CH2:13][CH:12]=[C:11]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][CH:7]=2)[CH2:16][CH2:15]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 5.0 gm (21.5 mMol) 6-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indole, 4.0 gm (23.6 mMol) N-(2-pyridinyl)-2-chloroacetamide and 4.45 gm (32 mMol) potassium carbonate in 25 mL dimethylformamide were heated to about 90° C. for 2 hours under nitrogen. The reaction mixture was concentrated under reduced pressure and was then partitioned between chloroform and water. The organic phase was separated, washed sequentially with water and saturated aqueous sodium chloride, dried over sodium sulfate and concentrated under reduced pressure. The residue was crystallized from ethanol to give 2.4 gm (30.4%) of the title compound as a yellow solid.

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customwas then partitioned between chloroform and water
customThe organic phase was separated
washwashed sequentially with water and saturated aqueous sodium chloride
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was crystallized from ethanol

Sources & evidence

ORD record: ord-e8ecc02a0aea434e8a6a7dc2ba4ec468
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05846982

Reaction notes

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