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

HRID 2114073ノート

反応式

HRID 2114073 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-9ecd6d82e4ff4caea8f528a1cd565513
出典データセット
uspto-grants-2008_10
特許番号
US07432375B2

反応ノート

読み込み中…