Sodium Carbonate → (1S)-2,2-difluoro-1-(3'-fluoro-5'-nitrobiphenyl-4-yl)ethanol

HRID 530397노트

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HRID 530397 반응식
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[C:4](I)[CH:3]=1.[F:12][CH:13]([F:25])[C@H:14]([C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1)[OH:15].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[F:12][CH:13]([F:25])[C@H:14]([C:16]1[CH:17]=[CH:18][C:19]([C:4]2[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=[C:2]([F:1])[CH:3]=2)=[CH:20][CH:21]=1)[OH:15]

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 2590861-Fluoro-3-iodo-5-nitrobenzeneHCID 129321750{4-[(1S)-2,2-difluoro-1-hydroxyethyl]phenyl}boronic acid

생성물 1

HCID 118307555(1S)-2,2-difluoro-1-(3'-fluoro-5'-nitrobiphenyl-4-yl)ethanol

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
85 °C

실험 절차

A mixture of PdCl2 (dppf)—dichloromethane adduct (40.8 mg, 0.050 mmol), 1-fluoro-3-iodo-5-nitrobenzene (267 mg, 1.00 mmol), {4-[(1S)-2,2-difluoro-1-hydroxyethyl]phenyl}boronic acid (222 mg, 1.10 mmol), sodium carbonate (1.50 mL, 3.00 mmol) and DMF (5 mL) was degassed by sparging with nitrogen and then heated to 85° C. for 3 hours. Upon cooling to room temperature, the reaction mixture was diluted with water, and aqueous NH4Cl, extracted with ethyl acetate, washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate/hexanes) to give (1S)-2,2-difluoro-1-(3′-fluoro-5′-nitrobiphenyl-4-yl)ethanol. MS ESI calc'd. for C14H11F3NO3[M+H]+ 298, found 298.

후처리

  1. customwas degassed
  2. customby sparging with nitrogen
  3. temperatureUpon cooling to room temperature
  4. additionthe reaction mixture was diluted with water, and aqueous NH4Cl
  5. extractionextracted with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-52bb75690a4e4006bb602cf7016a4353
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09353066B2

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