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

HRID 876444ノート

反応式

HRID 876444 の反応式
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]

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-23ee5b9c2efa4d36acbbc12742bb08a1
出典データセット
uspto-grants-2015_03
特許番号
US08987251B2

反応ノート

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