7-Chlorothieno[3,2-b]pyridine → 2-(6-(1,3-Dioxan-2-yl)pyridin-3-yl)-7-chlorothieno[3,2-b]pyridine

HRID 1400897노트

반응식

HRID 1400897 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[CH:9][S:10][C:3]=12.[Li]CCCC.Br[C:17]1[CH:18]=[CH:19][C:20]([CH:23]2[O:28][CH2:27][CH2:26][CH2:25][O:24]2)=[N:21][CH:22]=1>C1COCC1.[Cl-].[Cl-].[Zn+2]>[O:24]1[CH2:25][CH2:26][CH2:27][O:28][CH:23]1[C:20]1[N:21]=[CH:22][C:17]([C:9]2[S:10][C:3]3[C:4](=[N:5][CH:6]=[CH:7][C:2]=3[Cl:1])[CH:8]=2)=[CH:18][CH:19]=1

참가 물질

6

반응물 3

HCID 112752517-Chlorothieno[3,2-b]pyridineHCID 584745645-Bromo-2-(1,3-dioxan-2-yl)pyridineHCID 178418339Butyllithium

생성물 1

HCID 584748922-(6-(1,3-Dioxan-2-yl)pyridin-3-yl)-7-chlorothieno[3,2-b]pyridine수율 59%

시약·촉매·용매 2

HCID 3007855Zincchloride촉매HCID 8028Tetrahydrofuran용매3회

실험 절차

To a stirred solution of 7-chlorothieno[3,2-b]pyridine (12.08 g, 71.2 mmol) in THF (138 mL) at −15° C. was added n-BuLi (30.7 mL, 77.0 mmol). After 30 min, a solution of ZnCl2 0.5 M in THF (142 mL, 71.2 mmol) was added at −15° C. and the reaction mixture was allowed to warm to RT over 45 min. A solution of palladium tetrakistriphenylphosphine (1.266 g, 1.096 mmol) and bromide 278 (13.37 g, 54.8 mmol) in THF (18.5 mL) was added and the mixture was heated to reflux for 2 h then concentrated. The residue was diluted with water and ammonium hydroxide and extracted with DCM. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. The residue was triturated with MTBE to afford the title compound 279 (10.70 g, 32.2 mmol, 59% yield) as light brown solid. MS (m/z): 333.33 (M+H).

후처리

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2 h
  3. concentrationthen concentrated
  4. additionThe residue was diluted with water and ammonium hydroxide
  5. extractionextracted with DCM
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was triturated with MTBE

출처 및 근거

ORD 기록
ord-d45fb2b9a1304b0fb4334e3338588d68
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906852B2

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