Triethylamine → 3-(Phenylthio)-1H-pyrrolo[2,3-b]pyridine

HRID 731559

反応式

HRID 731559 の反応式
[C:1]1([S:7]([CH3:9])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[NH:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][N:30]=2)C=[CH:24]1.C(N(CC)CC)C>C(Cl)Cl>[C:1]1([S:7][C:9]2[C:26]3[C:31](=[N:30][CH:29]=[CH:28][CH:27]=3)[NH:23][CH:24]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 92221H-Pyrrolo(2,3-b)pyridineHCID 9845Trifluoroacetic anhydrideHCID 14516Methyl phenyl sulfoxide

生成物 1

HCID 220281883-(Phenylthio)-1H-pyrrolo[2,3-b]pyridine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
-78 °C

実験手順

A solution of methyl phenyl sulfoxide (8.33 g, 59.4 mmol) in CH2Cl2 is chilled to −78° C. and treated dropwise with trifluoroacetic anhydride (4.1 mL, 5.3 mmol). After stirring for 30 min at −78° C., a solution of 7-azaindole (5.2 g, 44.0 mmol) in CH2Cl2 is added. After 30 min at −78° C., triethylamine (74 mL, 534 mmol) is added and the reaction is allowed to reach ambient temperature. After stirring for 3.5 days, the reaction is concentrated in vacuo, treated with saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic extracts are combined and concentrated in vacuo. The resultant residue is crystallized from methanol/H2O and recrystallized from CH2Cl2/hexane to afford the title compound as an off-white solid, 1.26 g, mp 188-189° C., characterized by mass spectral analyses and HNMR analyses.

後処理

  1. waitAfter 30 min at −78° C.
  2. customto reach ambient temperature
  3. stirringAfter stirring for 3.5 days
  4. concentrationthe reaction is concentrated in vacuo
  5. additiontreated with saturated aqueous NaHCO3
  6. extractionextracted with CH2Cl2
  7. concentrationconcentrated in vacuo
  8. customThe resultant residue is crystallized from methanol/H2O
  9. customrecrystallized from CH2Cl2/hexane

出典と根拠

ORDレコード
ord-1ebe59d767eb40b0a6478d896c2d0186
出典データセット
uspto-grants-2009_09
特許番号
US07585873B2

関連ノート

読み込み中…