Phosphorus oxychloride → HCID 58608149, compound

HRID 2243572Notes

Reaction equation

HRID 2243572 reaction equation
C([N:8]1[CH:13]=[CH:12][C:11](=O)[C:10]2[C:15]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[CH:20][CH:19]=3)[O:17][C:9]1=2)C1C=CC=CC=1.P(Cl)(Cl)([Cl:41])=O>>[Cl:41][C:11]1[CH:12]=[CH:13][N:8]=[C:9]2[O:17][C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][O:30][CH2:29][CH2:28]4)=[CH:20][CH:19]=3)=[C:15]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[C:10]=12

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 58608125HCID 58608125, compound

Product 1

HCID 58608149HCID 58608149, compound

Conditions

Temperature
110 °C

Procedure

A resealable tube was charged with 7-benzyl-2-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-3-phenyl-7H-furo[2,3-b]pyridin-4-one (4c) (0.100 g, 0.197 mmol) and phosphorous oxychloride (2.0 mL). The system was flushed with argon and the tube was sealed. The mixture stirred at 110° C. for 1.5 h. The reaction mixture was concentrated, and the residue was partitioned between dichloromethane and ice water. The aqueous phase was separated and extracted with dichloromethane. The combined organic phases were washed with saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered, and concentrated to afford an orange brown oil. This oil was purified via preparative thin layer chromatography (eluting with 90:10:1, dichloromethane/methanol/ammonium hydroxide) to afford 4-chloro-2-[4-(2-morpholin-4-yl-ethoxy)-phenyl]-3-phenyl-furo[2,3-b]pyridine 6c as an off white solid. MS (MH+) 435.0; Calculated 434 for C25H23ClN2O3.

Workup

  1. customThe system was flushed with argon
  2. customthe tube was sealed
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was partitioned between dichloromethane and ice water
  5. customThe aqueous phase was separated
  6. extractionextracted with dichloromethane
  7. washThe combined organic phases were washed with saturated aqueous sodium bicarbonate solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto afford an orange brown oil
  12. customThis oil was purified via preparative thin layer chromatography (eluting with 90:10:1, dichloromethane/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-5ef321cf80ce44bf963c4aefcf5e5b96
Source dataset
uspto-grants-2010_03
Patent number
US07674907B2

Reaction notes

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