Nitrogen → 6-Acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-carbonitrile

HRID 510819노트

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HRID 510819 반응식
FC(F)(F)S(O[C:7]1[C:12]([C:13](=[O:15])[CH3:14])=[CH:11][C:10]([Cl:16])=[C:9]([CH3:17])[C:8]=1[C:18]#[N:19])(=O)=O.[F:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[CH:27][CH:28]=1.N#N>C1(C)C=CC=CC=1.C(=O)(O)[O-].[Na+].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>[C:13]([C:12]1[CH:11]=[C:10]([Cl:16])[C:9]([CH3:17])=[C:8]([C:18]#[N:19])[C:7]=1[C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([F:22])[CH:28]=1)(=[O:15])[CH3:14]

참가 물질

7

반응물 3

HCID 947NitrogenHCID 27339863-Fluorophenylboronic acidHCID 583686446-Acetyl-4-chloro-2-cyano-3-methylphenyl trifluoromethanesulfonate

생성물 1

HCID 583684696-Acetyl-4-chloro-3'-fluoro-3-methylbiphenyl-2-carbonitrile수율 99%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 516892Sodium Bicarbonate용매

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온도
80 °C

실험 절차

A biphasic solution of 6-acetyl-4-chloro-2-cyano-3-methylphenyl trifluoromethanesulfonate (2.54 g, 7.4 mmol) and (3-fluorophenyl)boronic acid (1.6 g, 11 mmol) in toluene (70 mL) and saturated sodium bicarbonate (70 mL) was bubbled with N2 to degas. After tetrakis(triphenylphosphine)palladium(0) (0.43 g, 0.37 mmol) was added, the mixture was bubbled with N2 for 5 min more and then heated at 80° C. for 2 hours. After cool to room temperature, the mixture was diluted with ethyl acetate. The layers were separated and the aq. layer was extracted with more ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. The residue was purified on silica gel column, eluting with 0 to 40% ethyl acetate in hexane, to give the desired product (2.1 g, 99%). LCMS calculated for C16H12ClFNO (M+H)+: m/z=288.1. found: 288.1.

후처리

  1. customto degas
  2. customthe mixture was bubbled with N2 for 5 min more
  3. temperatureAfter cool to room temperature
  4. additionthe mixture was diluted with ethyl acetate
  5. customThe layers were separated
  6. extractionthe aq. layer was extracted with more ethyl acetate
  7. washThe combined extracts were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe residue was purified on silica gel column
  12. washeluting with 0 to 40% ethyl acetate in hexane

출처 및 근거

ORD 기록
ord-900856663b4b420ca7875ac472ae52b9
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096600B2

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