Pyridine → 7-oxo-7H-thieno[3,2-b]pyridine-4,6-dicarboxylic acid 6-ethyl ester 4-isopropyl ester

HRID 2378096Notes

Reaction equation

HRID 2378096 reaction equation
N1C=CC=CC=1.[CH2:7]([O:9][C:10]([C:12]1[C:13]([OH:21])=[C:14]2[S:20][CH:19]=[CH:18][C:15]2=[N:16][CH:17]=1)=[O:11])[CH3:8].Cl[C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24]>ClCCl>[CH:26]([O:25][C:23]([N:16]1[CH:17]=[C:12]([C:10]([O:9][CH2:7][CH3:8])=[O:11])[C:13](=[O:21])[C:14]2[S:20][CH:19]=[CH:18][C:15]1=2)=[O:24])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7917Isopropyl chloroformateHCID 178469639HCID 178469639, compound

Product 1

HCID 589267297-oxo-7H-thieno[3,2-b]pyridine-4,6-dicarboxylic acid 6-ethyl ester 4-isopropyl esterYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add pyridine (1.20 ml, 14.8 mmol) to a suspension of 7-hydroxy-thieno[3,2-b]pyridine-6-carboxylic acid ethyl ester (1.10 g, 4.93 mmol) in dichloromethane (50 ml), and then add isopropyl chloroformate (1.0 N in toluene, 14.8 ml). Stir the reaction mixture at room temperature overnight. Wash the mixture with 1 N HCl (50 ml) followed by brine (3×50 ml). Separate the organic layer, dry over sodium sulfate, filter and concentrate. Purify using silica gel column chromatography (gradient eluent, 0-60% ethyl acetate in hexane) to provide 7-oxo-7H-thieno[3,2-b]pyridine-4,6-dicarboxylic acid 6-ethyl ester 4-isopropyl ester (1.37 g, 90%) as a white crystalline solid. MS (ES+): 310 (M+H).

Workup

  1. washWash the mixture with 1 N HCl (50 ml)
  2. customSeparate the organic layer
  3. dry with materialdry over sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify

Sources & evidence

ORD record
ord-f6645b56de4042eb9bfd163f76aed49a
Source dataset
uspto-grants-2008_12
Patent number
US07470705B2

Reaction notes

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