Triethylamine → Diethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate

HRID 2093088Notes

Reaction equation

HRID 2093088 reaction equation
Cl[C:2]1[CH2:3][CH2:4][N:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][C:7]=1[CH:8]=O.C(N(CC)CC)C.[C:22]([O:26][CH2:27][CH3:28])(=[O:25])[CH2:23][SH:24].[OH-].[K+]>N1C=CC=CC=1.O>[S:24]1[C:2]2[CH2:3][CH2:4][N:5]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:6][C:7]=2[CH:8]=[C:23]1[C:22]([O:26][CH2:27][CH3:28])=[O:25]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 14797Potassium HydroxideHCID 3024580Ethyl 4-chloro-3-formyl-5,6-dihydro-2H-pyridine-1-carboxylate

Product 1

HCID 14254905Diethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1049PyridineSolvent

Procedure

To a solution of ethyl 4-chloro-5-formyl-3,6-dihydropyridine-1(2H)-carboxylate (1 eq) obtained from step II in pyridine was added triethyl amine (1.5 eq.), ethyl thioglycolate (1 eq.) at 0° C. and the reaction mixture was stirred for overnight. A solution of KOH (1.5 eq) in water was added at 0° C. and further stirred at room temperature for 1 h Water was added and the organic layer was separated, dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford crude product, which, on purification by column chromatography afforded the desired diethyl 6,7-dihydrothieno[3,2-c]pyridine-2,5(4H)-dicarboxylate.

Workup

  1. additionwas added
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford crude product, which
  6. customon purification by column chromatography

Sources & evidence

ORD record
ord-93ba4230e1124f93a0d1de608bdd39eb
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

Loading…