Ethanol → 2-Methyl-1'H,2H-3,4'-bipyrazole

HRID 238370ノート

反応式

HRID 238370 の反応式
I[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][CH:3]=1.C(OC([N:15]1[CH:19]=[C:18](B(O)O)[CH:17]=[N:16]1)=O)(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>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.O.C1(C)C=CC=CC=1>[CH3:7][N:6]1[C:2]([C:18]2[CH:19]=[N:15][NH:16][CH:17]=2)=[CH:3][CH:4]=[N:5]1

参加物

8

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 133340655-Iodo-1-methyl-1H-pyrazoleHCID 441186751-tert-Butoxycarbonyl-1H-pyrazole-4-boronic acid

生成物 1

HCID 1363877762-Methyl-1'H,2H-3,4'-bipyrazole収率 32.9%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

Under a nitrogen atmosphere, a mixture of 5-iodo-1-methyl-1H-pyrazole (750 mg), [1-(tert-butoxycarbonyl)-1H-pyrazol-4-yl]boronic acid (1.27 g), tetrakis(triphenylphosphine)palladium(0) (209 mg), 2 M sodium carbonate aqueous solution (3.6 mL), ethanol (3.6 mL) and toluene (7.2 mL) was stirred at 100° C. for 14 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and was then concentrated under a reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=4:1 to 0:10), so as to obtain the title compound (176 mg) in the form of a light yellow solid.

後処理

  1. extractionthe obtained mixture was then extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationwas then concentrated under a reduced pressure
  4. customThe residue was purified by column chromatography (silica gel cartridge, hexane:ethyl acetate=4:1 to 0:10)

出典と根拠

ORDレコード
ord-a540602f3ca5468981ff4c7803c95013
出典データセット
uspto-grants-2014_02
特許番号
US08642626B2

反応ノート

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