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

HRID 2366220ノート

反応式

HRID 2366220 の反応式
[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

参加物

6

反応物 4

HCID 1049PyridineHCID 8471TriethylamineHCID 2723790ThioureaHCID 86668998HCID 86668998、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-59b698bf1f0c4408ba770ba0f95c2f48
出典データセット
uspto-grants-2014_04
特許番号
US08697708B2

反応ノート

読み込み中…