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

HRID 387968Notes

Reaction equation

HRID 387968 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-0933efe97f1947f8b594f275bdf60e99
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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