Potassium Phosphate, Tribasic → 8-(Tert-butyldimethylsilyloxy)-2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline

HRID 2035609노트

반응식

HRID 2035609 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[CH:20]=[CH:19][C:18]4[C:13](=[C:14]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH:15]=[CH:16][CH:17]=4)[N:12]=3)=[N:9][N:10]=2)[CH:7]=1.[CH:29]1(B(O)O)[CH2:31][CH2:30]1.P(C1CCCCC1)(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].O>[Si:22]([O:21][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]=1[N:12]=[C:11]([C:8]1[N:6]3[CH:7]=[C:2]([CH:29]4[CH2:31][CH2:30]4)[CH:3]=[CH:4][C:5]3=[N:10][N:9]=1)[CH:20]=[CH:19]2)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 672305262-(6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-(tert-butyldimethylsilyloxy)quinoline

생성물 1

HCID 672305218-(Tert-butyldimethylsilyloxy)-2-(6-cyclopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinoline수율 34.8%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매2회

실험 절차

2-(6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-(tert-butyldimethylsilyloxy)quinoline (0.500 g, 1.10 mmol), cyclopropylboronic acid (0.123 g, 1.43 mmol), Pd(OAc)2 (0.012 g, 0.0549 mmol), P(Cy)3 (0.031 g, 0.110 mmol), and K3PO4 (0.699 g, 3.29 mmol) were combined with 5.5 mL toluene and 0.55 mL H2O (both degassed with nitrogen 30 minutes prior to use). The mixture was sonicated and put on a 100° C. reaction block and stirred for 3 hours. The reaction mixture was cooled to ambient temperature, diluted with toluene, vacuum filtered through compressed Celite, rinsed with toluene, and the filtrate was concentrated. The crude material was purified on silica (5% to 60% ethyl acetate in dichloromethane) to give the title compound (0.159 g, 0.382 mmol, 34.8% yield) as a brown foam.

후처리

  1. customboth degassed with nitrogen 30 minutes
  2. customThe mixture was sonicated
  3. customput on a 100° C.
  4. customreaction block
  5. filtrationfiltered
  6. washrinsed with toluene
  7. concentrationthe filtrate was concentrated
  8. customThe crude material was purified on silica (5% to 60% ethyl acetate in dichloromethane)

출처 및 근거

ORD 기록
ord-7938f92d242a40d694bc4d7e9b339110
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575145B2

반응 노트

불러오는 중…