Water → HCID 77174865, compound

HRID 2361098Notes

Reaction equation

HRID 2361098 reaction equation
[C:1]1([C:7]2[C:12]3[CH:13]=[CH:14][O:15][C:11]=3[C:10](O)=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.O.O=P(Cl)(Cl)[Cl:26]>>[Cl:26][C:10]1[C:11]2[O:15][CH:14]=[CH:13][C:12]=2[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:8][N:9]=1

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 178518896HCID 178518896, compound

Product 1

HCID 77174865HCID 77174865, compound

Procedure

A slurry of 4-phenylfuro[3,2-d]pyridazin-7-ol (0.327 g, 1.5 mmol) and pyridine (0.38 ml, 4.6 mmol) in 5 mL POCl3 was heated with a water-cooled reflux condenser with drying tube to 130° C. for 3 h. The brown solution was cooled and the reaction judged complete by LCMS. The reaction was poured onto ice with stirring. The solution was neutralized with 6 N NaOH and ice to control temperature. The resulting mixture was extracted into DCM (3×). The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The solid was adsorbed onto 2 g silica gel from DCM/MeOH and dried. The material was purified by silica gel chromatography, eluting with 0-20% EtOAc/DCM to give 7-chloro-4-phenylfuro[3,2-d]pyridazine as an off-white solid. MS m/z=231 [M+H]+. Calc'd for C12H7ClN2O: 230.7.

Workup

  1. temperaturecooled
  2. temperaturereflux condenser
  3. customwith drying tube to 130° C. for 3 h
  4. temperatureThe brown solution was cooled
  5. additionThe reaction was poured onto ice
  6. extractionThe resulting mixture was extracted into DCM (3×)
  7. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customdried
  11. customThe material was purified by silica gel chromatography
  12. washeluting with 0-20% EtOAc/DCM

Sources & evidence

ORD record
ord-57f2f1ad82354ce58d9953477f71fcc4
Source dataset
uspto-grants-2014_04
Patent number
US08686155B2

Reaction notes

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