Thionyl Chloride → 3-(4-Fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester

HRID 1465952Notes

Reaction equation

HRID 1465952 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[N:10](CC2C=CC(OC)=CC=2OC)[CH2:9][C:8]2[C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:23][S:24][C:7]=2[C:6]1=[O:32])=[O:4].S(Cl)(Cl)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:10]=[CH:9][C:8]2[C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:23][S:24][C:7]=2[C:6]=1[OH:32])=[O:4]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 672335175-(2,4-Dimethoxy-benzyl)3-(4-fluoro-phenyl)-7-oxo-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester

Product 1

HCID 672328323-(4-Fluoro-phenyl)-7-hydroxy-thieno[3,2-c]pyridine-6-carboxylic acid methyl esterYield 61.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(2,4-dimethoxy-benzyl)-3-(4-fluoro-phenyl)-7-oxo-4,5,6,7-tetrahydro-thieno[3,2-c]pyridine-6-carboxylic acid methyl ester (0.39 g, 0.86 mmol), example 31-e, was dissolved in 6 mL of anhydrous dichloromethane. To the solution was added 93.7 μL of thionyl chloride, and the reaction mixture was stirred for 5 hours. The solution was filtered on a fine glass frit filter to collect a white solid precipitate. The solid was washed twice with cold dichloromethane and then partitioned between saturated sodium bicarbonate solution and ethyl acetate. The organic fraction was washed with brine, dried over anhydrous sodium sulfate, and concentrated to produce 0.16 g of a white solid. MS: (+) m/z 304.0 (M+1)

Workup

  1. filtrationThe solution was filtered on a fine glass frit
  2. filtrationfilter
  3. customto collect a white solid precipitate
  4. washThe solid was washed twice with cold dichloromethane
  5. custompartitioned between saturated sodium bicarbonate solution and ethyl acetate
  6. washThe organic fraction was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f646457a525e49aba8c65efac2322d41
Source dataset
uspto-grants-2015_04
Patent number
US09000006B2

Reaction notes

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