Methyl iodide → 5-tert-Butyl 2-methyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate

HRID 2301113Notes

Reaction equation

HRID 2301113 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([C:17]([OH:19])=[O:18])=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:20](=O)([O-])[O-].[K+].[K+].CI.C(OCC)(=O)C>CN(C)C=O>[CH3:20][O:18][C:17]([C:15]1[S:14][C:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][C:10]=2[CH:16]=1)=[O:19]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 177503995-(tert-Butoxycarbonyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylic acid

Product 1

HCID 665232235-tert-Butyl 2-methyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-t-Butoxycarbonyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-2-carboxylic acid (300 mg, 1.1 mmol), potassium carbonate (150 mg, 1.1 mol) and methyl iodide (150 mg, 1.1 mmol) were stirred at room temperature for 4.5 hours in anhydrous N,N-dimethylformamide (3 ml). The reaction solution was mixed with ethyl acetate, washed with water and saturated brine and then dried with anhydrous sodium sulfate to obtain crude 5-t-butoxycarbonyl-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-2-carboxylic acid methyl ester. This was mixed with hydrochloric acid-saturated methanol (4 ml) and stirred at room temperature for 14 hours. By evaporating the solvent from the reaction solution under a reduced pressure, crude 4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-2-carboxylic acid methyl ester hydrochloride was obtained. This compound and triethylamine (0.59 ml, 4.2 mmol) and 2a-(4-bromobutyl)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one (310 mg, 1.0 mmol) were stirred at room temperature for 24 hours in anhydrous N,N-dimethylformamide (10 ml). The reaction solution was mixed with ethyl acetate, washed with water and saturated brine and then dried with anhydrous sodium sulfate. The solvent was removed by evaporation under a reduced pressure, and the thus obtained material was separated and purified by a silica gel column chromatography to obtain 240 mg (0.56 mmol, 56% in yield) of the title compound.

Workup

  1. washwashed with water and saturated brine
  2. dry with materialdried with anhydrous sodium sulfate

Sources & evidence

ORD record
ord-c865a16dde1a48c2bd059b4b766f8eee
Source dataset
uspto-grants-2002_12
Patent number
US06498251B1

Reaction notes

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