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

HRID 2253386ノート

反応式

HRID 2253386 の反応式
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

参加物

7

反応物 4

HCID 962Water2 回HCID 17749109Barium hydroxide, octahydrateHCID 21084187tert-butyl N-[7-bromo-2-(methoxymethyl)pyrazolo[1,5-a]pyridin-3-yl]carbamateHCID 230809452,6-Dimethoxy-4-methoxymethylphenylboric acid

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3d56129d2b65433987a215b88547beee
出典データセット
uspto-grants-2008_01
特許番号
US07323569B2

反応ノート

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