Potassium Carbonate → 4-(3-Naphthalen-1-ylmethyl-2,3-dihydro-imidazo[1,2-a]pyridin-2-ylsulfanyl)-butyric acid methyl ester

HRID 215969Notes

Reaction equation

HRID 215969 reaction equation
[C:1]1([CH2:11][CH:12]2[N:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]3=[N:14][C:13]2=[S:21])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Br[CH2:23][CH2:24][CH2:25][C:26]([O:28][CH3:29])=[O:27].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.ClCCl>[CH3:29][O:28][C:26](=[O:27])[CH2:25][CH2:24][CH2:23][S:21][CH:13]1[CH:12]([CH2:11][C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)[N:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]2=[N:14]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 107604Methyl 4-bromobutyrateHCID 59176770HCID 59176770, compound

Product 1

HCID 687023894-(3-Naphthalen-1-ylmethyl-2,3-dihydro-imidazo[1,2-a]pyridin-2-ylsulfanyl)-butyric acid methyl ester

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 75 mg (0.26 mmol) of 3-naphthalen-1-ylmethyl-imidazo[1,2-a]pyridine-2-thione and 70 mg (0.39 mmol) of methyl 4-bromobutyrate and 72 mg (0.52 mmol) of potassium carbonate in 3 mL of 50% acetone in dichloromethane is stirred at room temperature for 18 h. The mixture is concentrated in vacuo and the residue is purified by flash chromatography on silica gel eluting with 50˜75% ethyl acetate in hexanes to give the desired compound.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe residue is purified by flash chromatography on silica gel eluting with 50˜75% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-0d0cbd16d6bc4d90817cfc4af95c9b47
Source dataset
uspto-grants-2012_06
Patent number
US08193214B2

Reaction notes

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