Sodium Carbonate → 2-Cyclopropyl-6-(trifluoromethyl)nicotinaldehyde

HRID 1626523ノート

反応式

HRID 1626523 の反応式
Cl[C:2]1[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH:14]1(B(O)O)[CH2:16][CH2:15]1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:14]1([C:2]2[N:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:3]=2[CH:4]=[O:5])[CH2:16][CH2:15]1

参加物

7

反応物 3

HCID 10340Sodium CarbonateHCID 2760897Cyclopropylboronic acidHCID 467399062-Chloro-6-(trifluoromethyl)pyridine-3-carbaldehyde

生成物 1

HCID 866644002-Cyclopropyl-6-(trifluoromethyl)nicotinaldehyde収率 71.9%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
90 °C

実験手順

2-Chloro-6-(trifluoromethyl)nicotinaldehyde (176 mg, 0.840 mmol), cyclopropylboronic acid (152 mg, 1.76 mmol), sodium carbonate (267 mg, 2.52 mmol) and tetrakis(triphenylphosphine)palladium (0) (48.5 mg, 0.0420 mmol) were combined, diluted with toluene (2 mL) and water (200 μL). The reaction vial was purged with argon, heated to 90° C. and stirred for 24 hours. The reaction was allowed to cool, loaded onto silica gel and eluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes to yield 2-cyclopropyl-6-(trifluoromethyl)nicotinaldehyde (130 mg, 0.604 mmol, 71.9% yield).

後処理

  1. customThe reaction
  2. customvial was purged with argon
  3. temperatureto cool
  4. washeluted with 5% ethyl acetate/hexanes to 50% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-2e9856b3cd7545e098d45477bcf06e59
出典データセット
uspto-grants-2014_07
特許番号
US08785445B2

反応ノート

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