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

HRID 925468노트

반응식

HRID 925468 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 722135923-Bromo-8-chloro-1,7-naphthyridine수율 67.8%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
130 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4615effa9530440cba8a79c65226ee5a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284284B2

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