Benzyl Bromide → 1-benzyl-1H-pyrrolo[3,2-b]pyridine

HRID 273315

반응식

HRID 273315 반응식
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C>[CH2:12]([N:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 92264-AzaindoleHCID 24758Sodium hydride

생성물 1

HCID 452673141-benzyl-1H-pyrrolo[3,2-b]pyridine수율 61.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

A solution of 1H-pyrrolo[3,2-b]pyridine (1.30 g, 9.42 mmol) in DMF (15 ml) was treated with sodium hydride (60% in mineral oil, 434 mg, 11.3 mmol) at r.t. until effervescence ceased. After cooling to 0° C. benzyl bromide (1.68 ml, 14.1 mmol) was added and the reaction warmed at 60° C. overnight. The reaction mixture was partitioned between water and EtOAc (50 ml each) and extracted with EtOAc (50 ml). The combined organics were washed with brine (20 ml), dried (MgSO4), filtered and concentrated in vacuo to give the title compound as a brown oil (1.20 g, 58%). δH (CDCl3) 8.39 (1H, d, J 4.4 Hz), 7.48 (1H, d, J 8.2 Hz), 7.30 (1H, d, J 3.1 Hz), 7.26-7.18 (3H, m), 7.04-6.69 (3H, m), 6.67 (1H, d, J 4.4 Hz), 5.11 (2H, s). LCMS (ES+) RT 1.56 ml 209 (M+H+).

후처리

  1. additionwas added
  2. customThe reaction mixture was partitioned between water and EtOAc (50 ml each)
  3. extractionextracted with EtOAc (50 ml)
  4. washThe combined organics were washed with brine (20 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3f233d2f3cda41a996d3f96e2a2c7045
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456286B2

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