Water → HCID 50991642, compound

HRID 240851Notes

Reaction equation

HRID 240851 reaction equation
Cl.Cl[CH2:3][CH2:4][N:5]([CH3:7])[CH3:6].C(=O)([O-])[O-].[Cs+].[Cs+].[OH:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:29]3[C:24](=[CH:25][C:26]([N:30]4[CH2:35][CH2:34][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:32][CH2:31]4)=[CH:27][CH:28]=3)[N:23]([C:43]3[CH:48]=[CH:47][N:46]=[CH:45][CH:44]=3)[CH:22]=2)=[CH:17][CH:16]=1.O>CN(C=O)C>[CH3:6][N:5]([CH3:7])[CH2:4][CH2:3][O:14][C:15]1[CH:16]=[CH:17][C:18]([C:21]2[C:29]3[C:24](=[CH:25][C:26]([N:30]4[CH2:31][CH2:32][N:33]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:34][CH2:35]4)=[CH:27][CH:28]=3)[N:23]([C:43]3[CH:44]=[CH:45][N:46]=[CH:47][CH:48]=3)[CH:22]=2)=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 50991641HCID 50991641, compound

Product 1

HCID 50991642HCID 50991642, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Chloro-N,N-dimethylethylamine hydrochloride (7.3 mg, 0.051 mmol) and cesium carbonate (33 mg, 0.101 mmol) were added to a mixture solution of tert-butyl 4-(3-(4-hydroxyphenyl)-1-(pyridin-4-yl)-1H-indol-6-yl)piperazine-1-carboxylate (12 mg, 0.025 mmol) in DMF (1 mL). After room temperature stirring at room temperature for 16 hours, followed by addition of water, the mixture was extracted with ethyl acetate. The collected organic layer was washed with brine and concentrated under reduced pressure by drying with anhydrous magnesium sulfate. The target compound was obtained as white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe collected organic layer was washed with brine
  3. concentrationconcentrated under reduced pressure
  4. dry with materialby drying with anhydrous magnesium sulfate
  5. customThe target compound was obtained as white solid

Sources & evidence

ORD record
ord-9780e54d46244fe4a0c408af0b55405c
Source dataset
uspto-grants-2014_02
Patent number
US08648089B2

Reaction notes

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