Sodium Carbonate → 2-(6-Phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol

HRID 2035612노트

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HRID 2035612 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](C(C)(C)C)(C)C)[CH:15]=[CH:16][CH:17]=4)[N:12]=3)=[N:9][N:10]=2)[CH:7]=1.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O1CCOCC1>[C:29]1([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8]([C:11]4[CH:20]=[CH:19][C:18]5[C:13](=[C:14]([OH:21])[CH:15]=[CH:16][CH:17]=5)[N:12]=4)=[N:9][N:10]=3)[CH:7]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 672305262-(6-Bromo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)-8-(tert-butyldimethylsilyloxy)quinoline

생성물 1

HCID 1363378092-(6-Phenyl-[1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol수율 37.1%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

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온도
110 °C

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), phenylboronic acid (0.167 g, 1.37 mmol), Pd(PPh3)4 (0.0634 g, 0.0549 mmol), and 2M aqueous Na2CO3 (2.74 mL, 5.49 mmol) (degassed with nitrogen 30 minutes prior to use) were combined with 7 mL dioxane (degassed with nitrogen 30 minutes prior to use), sonicated, and heated to 110° C. in a reaction block for 18 hours, during which the reaction went dry. The reaction mixture was cooled to ambient temperature, diluted with DMF, and the suspension was vacuum filtered through compressed Celite, rinsed with DMF, and the filtrate was concentrated. The crude material was purified on silica gel (1-20% methanol in dichloromethane gradient) to give the title compound (0.138 g, 0.408 mmol, 37.1% yield) as a brown solid.

후처리

  1. customdegassed with nitrogen 30 minutes
  2. customsonicated
  3. customwent dry
  4. temperatureThe reaction mixture was cooled to ambient temperature
  5. additiondiluted with DMF
  6. filtrationfiltered
  7. washrinsed with DMF
  8. concentrationthe filtrate was concentrated
  9. customThe crude material was purified on silica gel (1-20% methanol in dichloromethane gradient)

출처 및 근거

ORD 기록
ord-f487020650f54d1baaac522d1db7ca53
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08575145B2

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