Dimethylformamide → 7-Chloro-3-iodo-2-phenyl-pyrano[2,3-b]pyridin-4-one

HRID 1037247Notes

Reaction equation

HRID 1037247 reaction equation
[I:1][C:2]1[C:3](=[O:19])[C:4]2[CH:9]=[CH:8][C:7](=O)[NH:6][C:5]=2[O:11][C:12]=1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CN(C=O)C.S(Cl)([Cl:27])=O>C(Cl)Cl>[Cl:27][C:7]1[N:6]=[C:5]2[O:11][C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:2]([I:1])[C:3](=[O:19])[C:4]2=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 866710233-Iodo-2-phenyl-8H-pyrano[2,3-b]pyridine-4,7-dione

Product 1

HCID 866710247-Chloro-3-iodo-2-phenyl-pyrano[2,3-b]pyridin-4-oneYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 3-iodo-2-phenyl-8H-pyrano[2,3-b]pyridine-4,7-dione (13 mg, 0.036 mmol) in DCM (3 mL) was added DMF (0.03 mL) and thionyl chloride (0.1 mL). The mixture was heated under reflux for 3 hours, followed by standing at RT for 6 days. Upon evaporation, the residue was subjected to flash chromatography (SiO2, gradient 10 to 25% ethyl acetate in cyclohexane) to afford the title compound (10 mg, 74%) as a colourless gum. LCMS (Method B): RT=4.35 min, [M+H]+=384/386.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3 hours
  3. customUpon evaporation

Sources & evidence

ORD record
ord-a300ed00d9224a04bf7b40d259d460b3
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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