Potassium Carbonate → 3'-(Cyanomethyl)-5-fluoro-2-methylbiphenyl-4-carbonitrile

HRID 75521ノート

反応式

HRID 75521 の反応式
Br[C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:11])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:18]([CH2:20][C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)#[N:19]>CN(C)C=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>[C:18]([CH2:20][C:21]1[CH:26]=[C:25]([C:2]2[CH:3]=[C:4]([F:11])[C:5]([C:6]#[N:7])=[CH:8][C:9]=2[CH3:10])[CH:24]=[CH:23][CH:22]=1)#[N:19]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27733443-Cyanomethylphenylboronic acidHCID 341754194-Bromo-2-fluoro-5-methylbenzonitrile

生成物 1

HCID 676069913'-(Cyanomethyl)-5-fluoro-2-methylbiphenyl-4-carbonitrile収率 91.1%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

Tetrakis(triphenylphosphine)palladium (10 mg, 0.1 mmol) was added into the solution of 4-bromo-2-fluoro-5-methylbenzonitrile (110 mg, 0.5 mmol), K2CO3 70% aqueous solution (1 mL) and 3-(cyanomethyl)phenylboronic acid (96 mg, 0.6 mmol) in 10 ml N,N-dimethyl formamide, the solution was heated at 150° C. under microwave condition for 20 minutes, and the reaction mixture was partitioned with 20 mL water and 50 mL ethyl acetate, the aqueous layer was extracted with ethyl acetate (100 mL×2), and the combined organic layer was washed by saturated solution of sodium bicarbonate, sodium chloride, and dried by sodium sulfate, and concentrated by give quantitative products 3′-(cyanomethyl)-5-fluoro-2-methylbiphenyl-4-carbonitrile 3 (114 mg, 88% yield, confirmed by LCMS: 251.10) without purification for next steps.

後処理

  1. customthe reaction mixture was partitioned with 20 mL water and 50 mL ethyl acetate
  2. extractionthe aqueous layer was extracted with ethyl acetate (100 mL×2)
  3. washthe combined organic layer was washed by saturated solution of sodium bicarbonate, sodium chloride
  4. dry with materialdried by sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-1de5a6f96c6c4dc4916563c43b261c6e
出典データセット
uspto-grants-2014_09
特許番号
US08835445B2

反応ノート

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