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

HRID 523074ノート

反応式

HRID 523074 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 899956037-Bromo-2-chloro-1,6-naphthyridine収率 95%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide触媒

反応条件

温度
80 °C

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-e88d3e9699f8475494a908bf0f4b31cc
出典データセット
uspto-grants-2016_05
特許番号
US09334286B2

反応ノート

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