Potassium Carbonate → 4-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridin-2-ylsulfanyl]-butyric acid methyl ester

HRID 215974Notes

Reaction equation

HRID 215974 reaction equation
[CH3:1][C:2]1[C:10]2[C:9]([CH2:11][CH:12]3[N:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]4=[N:14][C:13]3=[S:21])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.Br[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[CH3:29][O:28][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][S:21][C:13]1[N:14]=[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]2[C:12]=1[CH2:11][C:9]1[C:10]2[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=2[S:7][CH:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 107604Methyl 4-bromobutyrateHCID 591767793-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridine-2-thione

Product 1

HCID 591767234-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridin-2-ylsulfanyl]-butyric acid methyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 472 mg (1.5 mmol) of 3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-imidazo[1,2-a]pyridine-2-thione and 407 mg (2.3 mmol) of methyl 4-bromobutyrate and 415 mg (3.0 mmol) of potassium carbonate in 5 mL of DMF is stirred at room temperature for 18 h. The mixture is diluted with water and the product is extracted with ethyl acetate. The organic layer is washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by flash chromatography on silica gel eluted with 1˜5% methanol in dichloromethane to give the desired compound.

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. washThe organic layer is washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography on silica gel
  7. washeluted with 1˜5% methanol in dichloromethane

Sources & evidence

ORD record
ord-a55fb718d9434d588052bb4ffe10f4b3
Source dataset
uspto-grants-2012_06
Patent number
US08193214B2

Reaction notes

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