1,4-Dioxane → 7-Chloro-3-(4-fluorophenyl)thieno[3,2-b]pyridine

HRID 593768노트

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HRID 593768 반응식
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][C:10]([Cl:11])=[C:5]2[S:4][CH:3]=1.[F:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.O1CCOCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Cl:11][C:10]1[CH:9]=[CH:8][N:7]=[C:6]2[C:2]([C:16]3[CH:17]=[CH:18][C:13]([F:12])=[CH:14][CH:15]=3)=[CH:3][S:4][C:5]=12

참가 물질

7

반응물 4

HCID 312751,4-DioxaneHCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 867304243-Bromo-7-chlorothieno[3,2-b]pyridine

생성물 1

HCID 867304237-Chloro-3-(4-fluorophenyl)thieno[3,2-b]pyridine수율 84.8%

시약·촉매·용매 2

HCID 178418807HCID 178418807, 화합물촉매HCID 962Water용매

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온도
90 °C

실험 절차

A vessel capable of sealing was charged with a mixture of 3-bromo-7-chlorothieno[3,2-b]pyridine (500 mg, 2.012 mmol), 4-fluorophenylboronic acid (310 mg, 2.213 mmol), PdCl2(dppf)-CH2Cl2 adduct (82 mg, 0.101 mmol), dioxane (8 mL), and a 2.0 M aqueous solution of K3PO4 (3 mL, 6.04 mmol) and was purged with nitrogen for 10 min. The vessel was sealed and heated at 90° C. for 1 h. Upon cooling, the reaction mixture was diluted with water and extracted with CH2Cl2. The combined organics were washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude material was purified by BIOTAGE® eluting with 40%-80% EtOAc/CH2Cl2 at 30 mL/min. Concentration of appropriate fractions provided the title compound (450 mg, 49% yield) as a white powder. LC/MS: Example 98A @ 3.62 min (RT) (Condition G). MS (ES): m/z=263.03, [M+H]+.

후처리

  1. customThe vessel was sealed
  2. temperatureUpon cooling
  3. extractionextracted with CH2Cl2
  4. washThe combined organics were washed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified by BIOTAGE®
  8. washeluting with 40%-80% EtOAc/CH2Cl2 at 30 mL/min

출처 및 근거

ORD 기록
ord-31fa6e13f2954e0b95da59d815679d06
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242967B2

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