Potassium Carbonate → 5-Amino-6-fluoro-4-methoxy-2-methylbiphenyl-3-carbonitrile

HRID 17525

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HRID 17525 반응식
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5](Br)([CH3:15])[CH:4]([C:17]#[N:18])[C:3]=1[O:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1.CB1OB(C)OB(C)O1>O.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>[NH2:1][C:2]1[C:3]([O:19][CH3:20])=[C:4]([C:17]#[N:18])[C:5]([CH3:15])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]=1[F:8]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 574072TrimethylboroxineHCID 685848335-Amino-2-bromo-6-fluoro-4-methoxy-2-methylbiphenyl-3-carbonitrile

생성물 1

HCID 860975095-Amino-6-fluoro-4-methoxy-2-methylbiphenyl-3-carbonitrile

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매2회HCID 962Water용매

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온도
110 °C

실험 절차

5-Amino-2-bromo-6-fluoro-4-methoxy-2-methylbiphenyl-3-carbonitrile (I-235) (2.02 g, 6.29 mmol), potassium carbonate (2.61 g, 18.87 mmol) and tetrakis(triphenylphosphine)palladium(0) (727 mg, 0.63 mmol) were dissolved in 10% water-containing 1,4-dioxane (50 ml), and at room temperature, trimethylboroxine (50 wt. % tetrahydrofuran solution, 1.90 ml, 7.55 mmol) was added. After stirring under nitrogen atmosphere at 110° C. for 8 hours and then cooling to room temperature, tetrakis(triphenylphosphine)palladium(0) (727 mg, 0.63 mmol) was added, followed by further stirring at 110° C. for 11 hours. After cooling to room temperature, the insoluble matter was separated by filtration, the filtrate was fractionated with ethyl acetate and saturated brine. The organic layer was separated, the aqueous layer was again extracted with ethyl acetate.

후처리

  1. temperaturecooling to room temperature
  2. stirringby further stirring at 110° C. for 11 hours
  3. temperatureAfter cooling to room temperature
  4. customthe insoluble matter was separated by filtration
  5. customThe organic layer was separated
  6. extractionthe aqueous layer was again extracted with ethyl acetate

출처 및 근거

ORD 기록
ord-41d3ba0b6a6148fcbd9992559d038a83
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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