Potassium Carbonate → 5-Methoxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine

HRID 2039826

반응식

HRID 2039826 반응식
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[CH:9]=[CH:10][NH:11][C:6]2=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].I[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[Cl-].[NH4+]>CS(C)=O.C/C(/O)=C/C(C)=O.C/C(/O)=C/C(C)=O.[Cu]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[CH:9]=[CH:10][N:11]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:6]2=[CH:7][N:8]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 11575IodobenzeneHCID 25517Ammonium ChlorideHCID 53243695-methoxy-1H-pyrrolo[3,2-b]pyridine

생성물 1

HCID 669221905-Methoxy-1-phenyl-1H-pyrrolo[2,3-c]pyridine수율 92.8%

시약·촉매·용매 2

HCID 5363992Copper, bis(2,4-pentanedionato-O,O')-, (SP-4-1)-촉매HCID 679Dimethyl Sulfoxide용매

반응 조건

온도
130 °C

실험 절차

To a mixture of 5-methoxy-1H-pyrrolo[2,3-c]pyridine (6.00 g, 40.5 mmol; cf. D. Mazéas et al., Heterocycles 50 (1999), 1065), copper(II) acetylacetonate (1.06 g, 4.05 mmol) and potassium carbonate (11.2 g, 81.0 mmol) in DMSO (63 ml) was added iodobenzene (4.99 ml, 44.6 mmol). The reaction mixture was stirred at 130° C. for 10 h. The mixture was then cooled to room temperature, and a solution of ammonium chloride (20% in water) was added. The mixture was filtered through celite and the filtrate extracted three times with EA. The organic layers were combined, dried over sodium sulfate, filtered and evaporated under reduced pressure. Column chromatography of the residue on silica gel (EA/HEP) gave 8.43 g of the title compound.

후처리

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationThe mixture was filtered through celite
  3. extractionthe filtrate extracted three times with EA
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-e243633102c74b388dd3499f3436c046
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580813B2

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