Phosphorus oxychloride → HCID 86609504, compound

HRID 639923Notes

Reaction equation

HRID 639923 reaction equation
O=P(Cl)(Cl)[Cl:3].[F:6][C:7]1[CH:8]=[C:9]([C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=4)[CH:21]=3)[C:16](O)=[N:15][C:14]=2[C:30]#[N:31])[CH:10]=[CH:11][CH:12]=1.C([O-])(O)=O.[Na+]>O>[Cl:3][C:16]1[C:17]2[C:22](=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:19][CH:18]=2)[C:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([F:6])[CH:8]=2)=[C:14]([C:30]#[N:31])[N:15]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 178510606HCID 178510606, compound

Product 1

HCID 86609504HCID 86609504, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

POCl3 (22 mg, 0.15 mmol) was added to 4-(3-fluorophenyl)-1-hydroxy-6-pyridin-2-ylisoquinoline-3-carbonitrile (50 mg, 0.15 mmol) neat. The resulting mixture was heated to 90° C. for 18 h. The reaction was cooled to room temperature and diluted with H2O (10 mL). This was brought to a pH of 9 with NaHCO3. The aqueous layer was extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4), filtered and concentrated to yield the title compound as a brown oil.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5ecc2c1aadac48f6ae11e8e0e263a120
Source dataset
uspto-grants-2010_04
Patent number
US07691879B2

Reaction notes

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