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

HRID 2039826

反応式

HRID 2039826 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 5363992Copper, bis(2,4-pentanedionato-O,O')-, (SP-4-1)-触媒HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e243633102c74b388dd3499f3436c046
出典データセット
uspto-grants-2013_11
特許番号
US08580813B2

関連ノート

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