HCID 53884272, compound → tert-butyl 2-formyl-4H,5H,6H,7H-thieno[3,2-c]pyridine-5-carboxylate

HRID 234137Notes

Reaction equation

HRID 234137 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([C:17](NCCC3C=CC(OCC(OCC)=O)=C(OCC(OCC)=O)C=3)=[O:18])=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2[S:14][C:15]([CH:17]=[O:18])=[CH:16][C:10]=2[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 53884272HCID 53884272, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 11845085tert-butyl 2-formyl-4H,5H,6H,7H-thieno[3,2-c]pyridine-5-carboxylateYield 197%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of the compound prepared in (a) (1.2 g) in dichloromethane (20 ml) was added pyridinium chlorochromate (1.1 g), and the mixture was stirred at room temperature for 4 hours. After the reaction mixture was filtered through FLORISIL, the filtrate was concentrated and purified by column chromatography on silica gel to give 1.07 g of the title compound from the fraction eluted with ethyl acetate:n-hexane=1:3 (yield, 89.8%).

Workup

  1. filtrationAfter the reaction mixture was filtered through FLORISIL
  2. concentrationthe filtrate was concentrated
  3. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-af1fdbe52b7a488298660e105693e446
Source dataset
uspto-grants-1997_01
Patent number
US05594004

Reaction notes

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