Pyridine → 4-Chloro-2-(2,6-dichloro-4-iodophenyl)thiazolo[5,4-c]pyridine

HRID 2366220노트

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HRID 2366220 반응식
[Cl:1][C:2]1[CH:18]=[C:17]([I:19])[CH:16]=[C:15]([Cl:20])[C:3]=1[C:4](Cl)=[N:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([Cl:12])[C:7]=1F.NC(N)=[S:23].N1C=CC=CC=1.C(N(CC)CC)C>C(O)(C)C>[Cl:12][C:8]1[C:7]2[S:23][C:4]([C:3]3[C:2]([Cl:1])=[CH:18][C:17]([I:19])=[CH:16][C:15]=3[Cl:20])=[N:5][C:6]=2[CH:11]=[CH:10][N:9]=1

참가 물질

6

반응물 4

HCID 1049PyridineHCID 8471TriethylamineHCID 2723790ThioureaHCID 86668998HCID 86668998, 화합물

생성물 1

HCID 866689974-Chloro-2-(2,6-dichloro-4-iodophenyl)thiazolo[5,4-c]pyridine수율 84%

시약·촉매·용매 1

HCID 3776Isopropanol용매

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온도
90 °C

실험 절차

A mixture of 2,6-dichloro-N-(2-chloro-3-fluoropyridin-4-yl)-4-iodobenzimidoyl chloride (2.94 g, 6.30 mmol), thiourea (1.93 g, 25.3 mmol) and pyridine (1.73 mL, 21.4 mmol) in isopropanol (25 mL) was heated to 90° C. for 3.5 hours. Triethylamine (5.3 mL, 37.8 mmol) was added and the resulting mixture was heated to 90° C. for a further 1.5 h. The reaction was cooled to room temperature and then concentrated under reduced pressure. The resultant residue was partitioned between DCM and water. The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure. The residue was triturated with MeOH and dried under reduced pressure to give the desired compound (2.33 g, 84% yield). 1H NMR (300 MHz, CDCl3): δ 8.52 (d, J=5.6 Hz, 1H), 7.98 (d, J=5.6 Hz, 1H), 7.90-7.81 (s, 2H).

후처리

  1. temperaturethe resulting mixture was heated to 90° C. for a further 1.5 h
  2. temperatureThe reaction was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customThe resultant residue was partitioned between DCM and water
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with MeOH
  9. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-59b698bf1f0c4408ba770ba0f95c2f48
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697708B2

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