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

HRID 17525

反応式

HRID 17525 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒2 回HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-41d3ba0b6a6148fcbd9992559d038a83
出典データセット
uspto-grants-2010_06
特許番号
US07737166B2

関連ノート

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