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

HRID 1626523노트

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HRID 1626523 반응식
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

참가 물질

7

반응물 3

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

생성물 1

HCID 866644002-Cyclopropyl-6-(trifluoromethyl)nicotinaldehyde수율 71.9%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 1140Toluene용매

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온도
90 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-2e9856b3cd7545e098d45477bcf06e59
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785445B2

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