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

HRID 877935

반응식

HRID 877935 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 13387N-methyl-2-pyrrolidone용매2회HCID 57417360Sodium chloride; water용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-2a62888913954fa18c61db75b334b7ad
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987454B2

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