Potassium Carbonate → Ethyl 3-[1-(p-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-3-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate

HRID 1975734Notes

Reaction equation

HRID 1975734 reaction equation
[Cl:1][C:2]1[CH:32]=[CH:31][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([OH:16])=[CH:13][CH:14]=3)[C:9]([S:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[C:8]2[CH2:22][C:23]([CH3:30])([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:4][CH:3]=1.Cl.[N:34]1[CH:39]=[CH:38][CH:37]=[C:36]([CH2:40]Cl)[CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:40][C:36]4[CH:35]=[N:34][CH:39]=[CH:38][CH:37]=4)=[CH:13][CH:14]=3)[C:9]([S:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[C:8]2[CH2:22][C:23]([CH3:30])([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:31][CH:32]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 19935664Ethyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-hydroxy-1H-indol-2-yl)-2,2-dimethylpropanoate

Product 1

HCID 19098331Ethyl 3-[1-(p-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-3-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A suspension of ethyl 3-[1-(4-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-hydroxyindol-2-yl]-2,2-dimethylpropionate (3.0 g; 6.5 mmol), prepared as in step 4, 3-picolyl chloride hydrochloride (1.1 g; 6.5 mmol), and powdered potassium carbonate (2.7 g; 19.5 mmol) in 20 mL dimethylformamide (DMF) was stirred at ambient temperature for 4 days. The reaction mixture was diluted with brine and extracted with ethyl acetate. The extracts were dried over magnesium sulfate and concentrated. The resulting residue was subjected to flash chromatography on silica gel (70% diethyl ether in hexane) to give ethyl 3-[1-(p-chlorobenzyl)-3-(1,1-dimethylethylthio)-5-(pyrid-3-ylmethoxy)indol-2-yl]-2,2-dimethylpropionate as a pale yellow oil containing a small amount of DMF.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extracts were dried over magnesium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ae03c2c065d0470dbc42dfeac182315a
Source dataset
uspto-grants-1994_02
Patent number
US05288743

Reaction notes

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