Phosphorus oxychloride → 7-Bromo-2-chloro-1,6-naphthyridine

HRID 523074노트

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HRID 523074 반응식
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=O)[NH:9]2)=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:15])=O>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([Cl:15])=[N:9]2)=[CH:4][N:3]=1

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 899957277-Bromo-1,6-naphthyridin-2(1H)-one

생성물 1

HCID 899956037-Bromo-2-chloro-1,6-naphthyridine수율 95%

시약·촉매·용매 1

HCID 6228Dimethylformamide촉매

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온도
80 °C

실험 절차

7-Bromo-1,6-naphthyridin-2(1H)-one (Preparation 67, 800 mg 3.55 mmole) was treated with phosphorus oxychloride (18 mL) and catalytic DMF (2 drops). The reaction was heated at 80° C. for 2.5 hours. The phosphorus oxychloride was evaporated and the residue was azeotroped with toluene (15 mL). The solid was partitioned between ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate solution (30 mL) with ice (10 g). The aqueous layer was washed with EtOAc, the organic layers combined, washed with sodium bicarbonate solution, brine, dried over sodium sulphate and concentrated in vacuo to afford the title compound (826 mg, 95%).

후처리

  1. customThe phosphorus oxychloride was evaporated
  2. customthe residue was azeotroped with toluene (15 mL)
  3. customThe solid was partitioned between ethyl acetate (50 mL) and saturated aqueous sodium bicarbonate solution (30 mL) with ice (10 g)
  4. washThe aqueous layer was washed with EtOAc
  5. washwashed with sodium bicarbonate solution, brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e88d3e9699f8475494a908bf0f4b31cc
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334286B2

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