Potassium Carbonate → 4-Methyl-5-nitro-2-phenylpyridine

HRID 2358162ノート

反応式

HRID 2358162 の反応式
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(OCC)(=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>[CH3:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=[C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 3453642-Chloro-4-methyl-5-nitropyridine

生成物 1

HCID 463150594-Methyl-5-nitro-2-phenylpyridine収率 88.2%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 2 g (11.59 mmol) of 2-chloro-4-methyl-5-nitropyridine, 1.41 g (11.59 mmol) of phenylboronic acid, 1.33 g (1.16 mmol) of tetrakis(triphenylphosphine)palladium and 4 g (28.97 mmol) of potassium carbonate suspended in 50 ml of degassed dioxane is refluxed for 12 hours. The mixture is then cooled, diluted with 50 ml of ethyl acetate, successively washed twice with 20 ml of water and then with 20 ml of saturated sodium chloride solution, dried over sodium sulfate, filtered and then concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica (eluents: heptane/ethyl acetate) and then recrystallized from an isopropanol/isopropyl ether mixture. 2.19 g of a yellow solid are thus isolated, and are used without further purification in the following synthesis.

後処理

  1. temperatureis refluxed for 12 hours
  2. temperatureThe mixture is then cooled
  3. washsuccessively washed twice with 20 ml of water
  4. dry with materialwith 20 ml of saturated sodium chloride solution, dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica (eluents: heptane/ethyl acetate)
  9. customrecrystallized from an isopropanol/isopropyl ether mixture

出典と根拠

ORDレコード
ord-731dfa73fdf5481284b83d74ed1d63ee
出典データセット
uspto-grants-2010_07
特許番号
US07763636B2

反応ノート

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