Water → tert-Butyl N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl)carbamate

HRID 347852

반응식

HRID 347852 반응식
Br[C:2]1[N:7]2[N:8]=[C:9]([CH2:19][O:20][CH3:21])[C:10]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:6]2[CH:5]=[CH:4][CH:3]=1.O.[CH3:23][O:24][C:25]1[CH:30]=[C:29]([CH2:31][O:32][CH3:33])[CH:28]=[C:27]([O:34][CH3:35])[C:26]=1OB(O)O.O.O.O.O.O.O.O.O.[OH-].[Ba+2].[OH-]>COCCOC.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>[CH3:35][O:34][C:27]1[CH:28]=[C:29]([CH2:31][O:32][CH3:33])[CH:30]=[C:25]([O:24][CH3:23])[C:26]=1[C:2]1[N:7]2[N:8]=[C:9]([CH2:19][O:20][CH3:21])[C:10]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[C:6]2[CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962Water2회HCID 17749109Barium hydroxide, octahydrateHCID 21084187tert-butyl N-[7-bromo-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]carbamateHCID 230809452,6-Dimethoxy-4-methoxymethylphenylboric acid

생성물 1

HCID 21084182tert-Butyl N-[7-[2,6-dimethoxy-4-(methoxymethyl)phenyl]-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl)carbamate수율 63.6%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
80 °C

실험 절차

To a solution of tert-butyl N-[7-bromo-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]carbamate (300 mg) dissolved in 1,2-dimethoxyethane (10 mL) and water (5 mL) was added 2,6-dimethoxy-4-methoxymethylphenylboric acid (323 mg), tetrakis(triphenylphosphine)palladium(0) (146 mg) and barium hydroxide octahydrate (398 mg), and the reaction mixture was heated and stirred for 2 hours at 80° C. under a nitrogen stream. Water was added to the obtained reaction mixture, the reaction mixture was extracted with ethyl acetate, and the organic extract was washed with brine. The obtained organic extract was dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography and the title compound (245 mg) was obtained as a light yellow amorphous solid from the n-hexane:ethyl acetate (1:1) fraction.

후처리

  1. temperaturethe reaction mixture was heated
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. extractionthe organic extract
  4. washwas washed with brine
  5. extractionThe obtained organic extract
  6. dry with materialwas dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-8f6d71eb0978460bbfc1f398e44ae35d
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07176216B2

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