Phosphorus oxychloride → 3-Bromo-8-chloro-1,7-naphthyridine

HRID 925468ノート

反応式

HRID 925468 の反応式
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:6](=O)[NH:7][CH:8]=[CH:9][C:10]=2[CH:11]=1.CCN(C(C)C)C(C)C.O=P(Cl)(Cl)[Cl:24]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[N:7][C:6]=2[Cl:24]

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 895006083-Bromo-1,7-naphthyridin-8-ol

生成物 1

HCID 722135923-Bromo-8-chloro-1,7-naphthyridine収率 67.8%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
130 °C

実験手順

3-Bromo-7H-[1,7]naphthyridin-8-one (1.5 g, 6.67 mmol) was suspended in toluene (20 ml). DIPEA (3.5 ml, 20 mmol) and POCl3 (1.8 ml, 20 mmol) were added and the reaction mixture was heated to 130° C. for 36 h. The reaction mixture was cooled to rt and partitioned between water (75 ml) and EtOAc (150 ml). The phases were separated and the aq phase was extracted twice with EtOAc (25 ml). The combined organic layer was washed with NaHCO3 solution and brine, treated with MgSO4 and filtered. The filtrated was concentrated to give the desired product as a beige solid (1.1 g, 4.52 mmol).

後処理

  1. temperatureThe reaction mixture was cooled to rt
  2. custompartitioned between water (75 ml) and EtOAc (150 ml)
  3. customThe phases were separated
  4. extractionthe aq phase was extracted twice with EtOAc (25 ml)
  5. washThe combined organic layer was washed with NaHCO3 solution and brine
  6. additiontreated with MgSO4
  7. filtrationfiltered
  8. concentrationThe filtrated was concentrated

出典と根拠

ORDレコード
ord-4615effa9530440cba8a79c65226ee5a
出典データセット
uspto-grants-2016_03
特許番号
US09284284B2

反応ノート

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