Toluene → HCID 68663305、化合物

HRID 452598ノート

反応式

HRID 452598 の反応式
I[C:2]1[N:6]2[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)CCC.C1(C)C=CC=CC=1>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>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[C:2]1[N:6]2[CH:7]=[C:8]([C:11]([O:13][CH3:14])=[O:12])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1

参加物

6

反応物 3

HCID 1140TolueneHCID 6077842-(Tributylstannyl)pyridineHCID 16413170Methyl 3-iodoimidazo[1,2-a]pyridine-6-carboxylate

生成物 1

HCID 68663305HCID 68663305、化合物収率 75.4%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of methyl 3-iodoimidazo[1,2-a]pyridine-6-carboxylate (1.00 g, 3.30 mmol), 2-(tri-n-butylstannyl)pyridine (2.44 mg, 6.62 mmol), tetrakis(triphenylphosphine)palladium(0) (381 mg, 0.33 mmol) and toluene (50 mL) was heated under reflux overnight. After cooling, the reaction mixture was diluted with ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=4/1-1/1) to give the title compound (630 mg, yield 75%) as colorless crystals.

後処理

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. temperatureAfter cooling
  4. washwashed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by basic silica gel column chromatography (hexane/ethyl acetate=4/1-1/1)

出典と根拠

ORDレコード
ord-009ae0fa7d9c44a6a445115fe32b5e1b
出典データセット
uspto-grants-2013_07
特許番号
US08492378B2

反応ノート

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