Sodium Carbonate → 3-Fluoro-5-methoxy-[1,1'-biphenyl]-4-carbonitrile

HRID 922389노트

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HRID 922389 반응식
Br[C:2]1[CH:9]=[C:8]([O:10][CH3:11])[C:5]([C:6]#[N:7])=[C:4]([F:12])[CH:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCO.CCOC(C)=O>[F:12][C:4]1[CH:3]=[C:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:9]=[C:8]([O:10][CH3:11])[C:5]=1[C:6]#[N:7]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 574422094-Bromo-2-fluoro-6-methoxybenzonitrile

생성물 1

HCID 867193543-Fluoro-5-methoxy-[1,1'-biphenyl]-4-carbonitrile수율 97.9%

시약·촉매·용매 3

HCID 702Ethanol촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A mixture of 4-bromo-2-fluoro-6-methoxybenzonitrile (2, 5.22 g, 22.7 mmol), phenylboronic acid (4.15 g, 34 mmol) and 2 M Na2CO3 (23 mL) in toluene (100 mL) was purged with N2 for 10 min. Pd(PPh4)3 (2.62 g, 27.7 mmol) and EtOH (5 drops) were added. The mixture was then heated under N2 in a sealed tube at 80° C. for 18 h. The mixture was cooled to room temperature, diluted with EtOAc (300 mL), filtered through celite, concentrated and purified by silica gel chromatography eluting with ethyl acetate in hexane (0-100%) to afford the title compound (5.05 g, 97%) as a white solid: 1H NMR (500 MHz, CDCl3) δ 7.57-7.55 (m, 2H), 7.50-7.23 (m, 3H), 7.01-6.99 (m, 1H), 6.93 (s, 1H), 3.95 (s, 3H).

후처리

  1. customwas purged with N2 for 10 min
  2. temperatureThe mixture was cooled to room temperature
  3. filtrationfiltered through celite,
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography
  6. washeluting with ethyl acetate in hexane (0-100%)

출처 및 근거

ORD 기록
ord-45247b0850884ec0865cfe97db91ac0b
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09278940B2

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