Potassium tert-butoxide → 5-Chloro-1H-pyrrolo[2,3-b]pyridine

HRID 877935

反応式

HRID 877935 の反応式
CC(C)([O-])C.[K+].[Cl:7][C:8]1[CH:9]=[C:10]([C:15]#[C:16][Si](C)(C)C)[C:11]([NH2:14])=[N:12][CH:13]=1>CN1CCCC1=O.[Cl-].[Na+].O>[Cl:7][C:8]1[CH:9]=[C:10]2[CH:15]=[CH:16][NH:14][C:11]2=[N:12][CH:13]=1

参加物

5

反応物 2

HCID 23665647Potassium tert-butoxideHCID 247294655-Chloro-3-((trimethylsilyl)ethynyl)pyridin-2-amine

生成物 1

HCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridine収率 41%

試薬・触媒・溶媒 2

HCID 13387N-methyl-2-pyrrolidone溶媒2 回HCID 57417360Sodium chloride; water溶媒

反応条件

温度
80 °C

実験手順

A solution of potassium tert-butoxide (36 g, 320 mmol) in N-methylpyrrolidone (70 ml) was heated to 80° C. under nitrogen. A solution of 5-chloro-3-(trimethyl-silanylethynyl)-pyridin-2-ylamine (2) (36 g, 160 mmol) in NMP (200 ml) was added dropwise via a dropping funnel. The reaction mixture was stirred at 80° C. for a further fifty minutes. The reaction mixture was allowed to cool to room temperature. Brine (500 ml) was added to the reaction mixture and extracted with diethyl ether (5×200 ml). The combined organics were washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography, using as eluent pentane/EtOAc 0% to 40%, and further recrystallised from cyclohexane to afford the title compound (10 g, 41%). 1H NMR (CDCl3) 6.5 (1H, s), 7.4 (1H, s), 8.0 (1H, s), 8.2 (1H, s), 10.4-10.6 (1H, brs). MS (ES+) 153.

後処理

  1. temperatureto cool to room temperature
  2. extractionextracted with diethyl ether (5×200 ml)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. customfurther recrystallised from cyclohexane

出典と根拠

ORDレコード
ord-2a62888913954fa18c61db75b334b7ad
出典データセット
uspto-grants-2015_03
特許番号
US08987454B2

関連ノート

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