3-Fluorobenzenesulfonyl Chloride → WAY 208466 dihydrochloride

HRID 731567노트

반응식

HRID 731567 반응식
[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]=[CH:6]1.[F:15][C:16]1[CH:17]=[C:18]([S:22]([Cl:25])(=[O:24])=[O:23])[CH:19]=[CH:20][CH:21]=1>[N+](C1C=CC=CC=1)([O-])=O.FC(S([O-])(=O)=O)(F)F.[Ag+]>[ClH:25].[ClH:25].[CH3:1][N:2]([CH3:14])[CH2:3][CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([S:22]([C:18]2[CH:19]=[CH:20][CH:21]=[C:16]([F:15])[CH:17]=2)(=[O:24])=[O:23])=[CH:6]1

참가 물질

5

반응물 2

HCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 22028178HCID 22028178, 화합물

생성물 1

HCID 22028182WAY 208466 dihydrochloride

시약·촉매·용매 2

HCID 76223Silver(I) trifluoromethanesulfonate촉매HCID 7416Nitrobenzene용매

반응 조건

온도
100 °C

실험 절차

A stirred solution of N,N-dimethyl-N-[2-(1H-pyrrolo[2,3-b]pyridin-1-yl)ethyl]amine (1.66 g, 8.8 mmol) in nitrobenzene is treated with 3-fluorophenylsulfonyl chloride (1.88 g, 9.7 mmol) under nitrogen, followed by silver trifluoromethylsulfonate (2.94 g, 11.4 mmol), heated to 100° C. for 22 h, cooled and filtered through a cotton plug. The filtrate is treated with water and saturated aqueous NaHCO3 and extracted with CH2Cl2. The extracts are combined, dried over MgSO4 and concentrated in vacuo. The resultant residue is chromatographed eluting with 2:98 concentrated NH4OH:ethanol, to afford the free amine of the title compound as a viscous oil which solidifies (1.25 g, 41%). The free amine is dissolved in warm ethanol, treated with 4M HCl in dioxane and filtered. The filtercake is dried to give the title product as a pale yellow solid, 1.07 g (29% yield), mp 191-192° C., identified by mass spectral and HNMR analyses.

후처리

  1. temperaturecooled
  2. filtrationfiltered through a cotton plug
  3. additionThe filtrate is treated with water and saturated aqueous NaHCO3
  4. extractionextracted with CH2Cl2
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue is chromatographed
  8. washeluting with 2:98 concentrated NH4OH

출처 및 근거

ORD 기록
ord-1c89d2e9d1e84eebafaa0a006f7958fe
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585873B2

반응 노트

불러오는 중…