Phosphorus oxychloride → HCID 59215154, compound

HRID 2244587Notes

Reaction equation

HRID 2244587 reaction equation
O=P(Cl)(Cl)[Cl:3].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16](O)[C:17]3[CH:18]=[CH:19][C:20]([C:24]([F:27])([F:26])[F:25])=[N:21][C:22]=3[CH:23]=2)=[CH:10][CH:9]=1>>[Cl:3][C:16]1[N:15]=[C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH3:6])=[CH:9][CH:10]=2)[CH:23]=[C:22]2[C:17]=1[CH:18]=[CH:19][C:20]([C:24]([F:27])([F:26])[F:25])=[N:21]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178488436HCID 178488436, compound

Product 1

HCID 59215154HCID 59215154, compoundYield 55%

Conditions

Temperature
100 °C

Procedure

POCl3 (3 mL) was added to 7-(4-methoxyphenyl)-2-trifluoromethyl-[1,6]naphthyridin-5-ol (Example 19) (125 mg, 0.4 mmol). The mixture was heated at 100° C. for 3 hours. The excess POCl3 was concentrated under reduced pressure. The residue was diluted with CH2Cl2, washed with sat. NaHCO3, dried over Na2SO4, and concentrated giving the title compound (73 mg, 55%) as an orange solid.

Workup

  1. concentrationThe excess POCl3 was concentrated under reduced pressure
  2. additionThe residue was diluted with CH2Cl2
  3. washwashed with sat. NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fbd5eff9ec52425a9cd8f434e295998a
Source dataset
uspto-grants-2010_03
Patent number
US07678911B2

Reaction notes

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