Toluene → 5-Bromo-2-(2-fluoropyridin-4-yl)benzonitrile

HRID 592235ノート

反応式

HRID 592235 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5](I)=[C:6]([CH:9]=1)[C:7]#[N:8].[F:11][C:12]1[CH:17]=[C:16](B(O)O)[CH:15]=[CH:14][N:13]=1.C([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1>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(O)C.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:16]2[CH:15]=[CH:14][N:13]=[C:12]([F:11])[CH:17]=2)=[C:6]([CH:9]=1)[C:7]#[N:8]

参加物

8

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 27833962-Fluoropyridine-4-boronic acidHCID 70208745-Bromo-2-iodobenzonitrile

生成物 1

HCID 584476735-Bromo-2-(2-fluoropyridin-4-yl)benzonitrile

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
120 °C

実験手順

To a sealed tube were added 5-bromo-2-iodobenzonitrile 206-1 (500 mg, 1.6 mmol), 2-fluoropyridin-4-ylboronic acid 205-4 (229 mg, 1.6 mmol), Pd(PPh3)4 (94 mg, 0.08 mmol), Na2CO3 (516 mg, 4.9 mmol), toluene (2 mL), H2O (2 mL) and ethanol (0.5 mL). The reaction mixture was stirred at 120° C. overnight. After cooling to room temperature, the solvents were evaporated and the residue was redissolved in water (5 ml) and extracted with ethyl acetate (8 mL×3). The combined organic phases were dried over Na2SO4, and concentrated. The residue was purified by silica gel flash chromatography and eluted with 15% ethyl acetate in hexane to give 5-bromo-2-(2-fluoropyridin-4-yl)benzonitrile 206-3. MS m/z 277.1 (M+1).

後処理

  1. temperatureAfter cooling to room temperature
  2. customthe solvents were evaporated
  3. dissolutionthe residue was redissolved in water (5 ml)
  4. extractionextracted with ethyl acetate (8 mL×3)
  5. dry with materialThe combined organic phases were dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel flash chromatography
  8. washeluted with 15% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-4516f268cc054dbaa06fe9f15595bafd
出典データセット
uspto-grants-2016_01
特許番号
US09238646B2

反応ノート

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