Triphenylphosphine → 3-[4-{3-Bromo-1-(1-[{2-(trimethylsilyl)ethoxy}methyl]-1H-benzo[d]imidazol-2-yl)propyl}phenyl]-1-ethyl-1H-pyrazolo[4,3-b]pyridine

HRID 573301노트

반응식

HRID 573301 반응식
[CH2:1]([N:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([CH:18]([C:22]3[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:25]4[CH:35]=[CH:36][CH:37]=[CH:38][C:24]=4[N:23]=3)[CH2:19][CH2:20]O)=[CH:14][CH:13]=2)=[N:4]1)[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C(=O)N([Br:65])C(=O)C1.C([O-])(O)=O.[Na+]>CN(C=O)C>[Br:65][CH2:20][CH2:19][CH:18]([C:15]1[CH:14]=[CH:13][C:12]([C:5]2[C:6]3=[N:7][CH:8]=[CH:9][CH:10]=[C:11]3[N:3]([CH2:1][CH3:2])[N:4]=2)=[CH:17][CH:16]=1)[C:22]1[N:26]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:32])([CH3:34])[CH3:33])[C:25]2[CH:35]=[CH:36][CH:37]=[CH:38][C:24]=2[N:23]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 866889713-[4-(1-Ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenyl]-3-(1-[{2-(trimethylsilyl)ethoxy]methyl}-1H-benzo[d]imidazol-2-yl)propan-1-ol

생성물 1

HCID 866889733-[4-{3-Bromo-1-(1-[{2-(trimethylsilyl)ethoxy}methyl]-1H-benzo[d]imidazol-2-yl)propyl}phenyl]-1-ethyl-1H-pyrazolo[4,3-b]pyridine수율 83.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 3-{4-(1-ethyl-1H-pyrazolo[4,3-b]pyridin-3-yl)phenyl}-3-(1-[(2-(trimethylsilyl)ethoxy)methyl]-1H-benzo[d]imidazol-2-yl)propan-1-ol (80 mg) and PPh3 (43.7 mg) in DMF (2 mL) was added NBS (27.0 mg) at room temperature. The mixture was stirred at room temperature under a dry atmosphere for 1 h. The mixture was neutralized with saturated NaHCO3 aqueous solution at 0° C. and extracted with AcOEt. The organic layer was separated, washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/AcOEt) to give the title compound (75 mg).

후처리

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/AcOEt)

출처 및 근거

ORD 기록
ord-4ccd111bbb8046ebbe19513a890ca7fd
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029536B2

반응 노트

불러오는 중…