Thionyl Chloride → 4-Chloro-furo[2,3-b]pyridine-2-carboxylic acid methyl ester

HRID 1010356Notes

Reaction equation

HRID 1010356 reaction equation
S(Cl)([Cl:3])=O.[CH3:5][O:6][C:7]([C:9]1[O:18][C:12]2[NH:13][CH:14]=[CH:15][C:16](=O)[C:11]=2[CH:10]=1)=[O:8]>CN(C)C=O>[CH3:5][O:6][C:7]([C:9]1[O:18][C:12]2=[N:13][CH:14]=[CH:15][C:16]([Cl:3])=[C:11]2[CH:10]=1)=[O:8]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 58931135Methyl 4-hydroxyfuro[2,3-B]pyridine-2-carboxylate

Product 1

HCID 589308884-Chloro-furo[2,3-b]pyridine-2-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After adding thionyl chloride (8.0 ml) and dimethylformamide (0.08 ml) to 4-oxo-4,7-dihydro-furo[2.3-b]pyridine-2-carboxylic acid methyl ester (2.0 g), the mixture was heated to reflux for 1 hour. After cooling, the mixture was concentrated under reduced pressure and the precipitated crystals were filtered out and washed with tetrahydrofuran and ethyl acetate to obtain the title compound (2.1 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 1 hour
  3. temperatureAfter cooling
  4. concentrationthe mixture was concentrated under reduced pressure
  5. filtrationthe precipitated crystals were filtered out
  6. washwashed with tetrahydrofuran and ethyl acetate

Sources & evidence

ORD record
ord-4309388fe56d4be6bd311c756aebc096
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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