Triethylamine → HCID 66864775, compound

HRID 2093079Notes

Reaction equation

HRID 2093079 reaction equation
Cl[C:2]1[CH2:7][CH2:6][N:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH2:4][C:3]=1[CH:18]=O.C(N(CC)CC)C.[C:27]([O:31][CH2:32][CH3:33])(=[O:30])[CH2:28][SH:29].[OH-].[K+]>N1C=CC=CC=1.O>[CH3:17][C:14]1[CH:13]=[CH:12][C:11]([S:8]([N:5]2[CH2:6][CH2:7][C:2]3[S:29][C:28]([C:27]([O:31][CH2:32][CH3:33])=[O:30])=[CH:18][C:3]=3[CH2:4]2)(=[O:9])=[O:10])=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12185Ethyl ThioglycolateHCID 14797Potassium HydroxideHCID 86650192HCID 86650192, compound

Product 1

HCID 66864775HCID 66864775, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a solution of a 4-chloro-1-[(4-methylphenyl)sulfonyl]-1,2,5,6-tetrahydropyridine-3-carbaldehyde (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 the reaction was continued at room temperature for 1 h Reaction was quenched with water 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 ethyl 5-[(4-methylphenyl)sulfonyl]-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-2-carboxylate.

Workup

  1. waitthe reaction was continued at room temperature for 1 h
  2. customReaction
  3. customwas quenched with water
  4. customthe organic layer was separated
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customto afford crude product, which
  8. customon purification by column chromatography

Sources & evidence

ORD record
ord-96574babf2e94fc1bba2530217d227f0
Source dataset
uspto-grants-2013_05
Patent number
US08440830B2

Reaction notes

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