1,2-Dimethoxyethane → 3-(3-Fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine

HRID 34085노트

반응식

HRID 34085 반응식
Br[C:2]1[C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:3]=1.[F:30][C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-].C(COC)OC>C(OCC)(=O)C.O.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>[F:30][C:31]1[CH:36]=[C:35]([C:2]2[C:6]3[CH:7]=[N:8][CH:9]=[CH:10][C:5]=3[N:4]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[N:3]=2)[CH:34]=[CH:33][CH:32]=1

참가 물질

8

반응물 4

HCID 80711,2-DimethoxyethaneHCID 27339863-Fluorophenylboronic acidHCID 17749109Barium hydroxide, octahydrateHCID 689284263-Bromo-1-trityl-1H-pyrazolo[4,3-c]pyridine

생성물 1

HCID 689269803-(3-Fluorophenyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine수율 93.6%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매2회HCID 8857Ethyl Acetate용매

실험 절차

A solution of 500 mg of 3-bromo-1-trityl-1H-pyrazolo[4,3-c]pyridine, 131 mg of 3-fluorophenylboronic acid, tetrakis(triphenylphosphine)palladium(0) and 537 mg of barium hydroxide octahydrate in a mixed solution of 18 mL of dimethoxyethane and 3 mL of water was stirred at 80° C. for 2 hours. The solution was diluted with ethyl acetate and water, followed by filtration through Celite. The organic layer of filtrate was washed with saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:3-dichloromethane:n-hexane=1:2-1:1-dichloromethane:methanol 100:1), to afford 399 mg of the title compound as colorless crystals.

후처리

  1. filtrationfollowed by filtration through Celite
  2. washThe organic layer of filtrate was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe crude product was purified
  6. customseparated by silica gel column chromatography (ethyl acetate:n-hexane=1:10-1:3-dichloromethane:n-hexane=1:2-1:1-dichloromethane:methanol 100:1)

출처 및 근거

ORD 기록
ord-6c6b997dc9104a30b0bda13765ea29c4
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429609B2

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