Phosphorus oxychloride → HCID 59215169, compound

HRID 2244589Notes

Reaction equation

HRID 2244589 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]=[C:19]([Br:24])[CH:20]=[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]=[C:19]([Br:24])[CH:20]=[N:21]2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178488433HCID 178488433, compound

Product 1

HCID 59215169HCID 59215169, compoundYield 94%

Conditions

Temperature
100 °C

Procedure

POCl3 (3 mL) was added to 7-(4-methoxyphenyl)-3-bromo-[1,6]naphthyridin-5-ol (Example 22) (115 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 5-chloro-7-(4-methoxyphenyl)-3-bromo-[1,6]naphthyridine (115 mg, 94%) as a yellow 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-5c8cf7f73e7048278823894913469179
Source dataset
uspto-grants-2010_03
Patent number
US07678911B2

Reaction notes

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