Dichloromethane → 5-Morpholin-4-yl-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 2114073노트

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HRID 2114073 반응식
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([N:19]4[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:18]=[C:13]3[C:12]([C:25]3[CH:26]=[N:27][NH:28][CH:29]=3)=[CH:11]2)(=O)=O)C=CC=CC=1.[OH-].[Na+].C(Cl)Cl>CCO>[N:19]1([C:17]2[CH:18]=[C:13]3[C:12]([C:25]4[CH:29]=[N:28][NH:27][CH:26]=4)=[CH:11][NH:10][C:14]3=[N:15][CH:16]=2)[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1

참가 물질

5

반응물 3

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 689732081-Benzenesulfonyl-5-morpholin-4-yl-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 598119155-Morpholin-4-yl-3-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine수율 78.2%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
90 °C

실험 절차

A mixture of 57 (0.031 g, 0.076 mmol) and 10% aqueous NaOH solution (1 mL) in EtOH (2 mL) was stirred at 90° C. for 1 hour. The mixture was cooled and evaporated to afford a tan syrup. The syrup was dissolved with CH2Cl2 and the solution was washed with brine. The aqueous layer was extracted twice with CH2Cl2. The combined extracts were dried (MgSO4) and concentrated to afford a syrup, which was purified by means of preparative TLC with CH2Cl2:MeOH as eluent to afford 58 (0.016 g, 78%) as a pale brown solid. 1H NMR (400 MHz, CD3OD) δ 3.13-3.17 (m, 4H), 3.85-3.89 (m, 4H), 7.51 (s, 1H), 7.74 (d, J=0.26 Hz, 1H), 7.93 (bs, 2H), 8.06 (d, J=0.26 Hz, 1H).

후처리

  1. temperatureThe mixture was cooled
  2. customevaporated
  3. customto afford a tan syrup
  4. washthe solution was washed with brine
  5. extractionThe aqueous layer was extracted twice with CH2Cl2
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. concentrationconcentrated
  8. customto afford a syrup, which
  9. customwas purified by means of preparative TLC with CH2Cl2

출처 및 근거

ORD 기록
ord-9ecd6d82e4ff4caea8f528a1cd565513
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07432375B2

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