Phosphorus oxychloride → HCID 59215169, compound

HRID 646599Notes

Reaction equation

HRID 646599 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-a94986e5c8d543abbb81209a34c37ce8
Source dataset
uspto-grants-2010_04
Patent number
US07705151B2

Reaction notes

Loading…