Toluene → Ethyl 2-(4-(2-methylpyridin-4-yl)phenyl)acetate

HRID 592130

反応式

HRID 592130 の反応式
[CH3:1][C:2]1[CH:7]=[C:6](B2OC(C)(C)C(C)(C)O2)[CH:5]=[CH:4][N:3]=1.I[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:19]=1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>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>[CH3:1][C:2]1[CH:7]=[C:6]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:20][CH:19]=2)[CH:5]=[CH:4][N:3]=1

参加物

7

反応物 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 14974990Ethyl (4-iodophenyl)acetateHCID 164142742-Methylpyridine-4-boronic acid pinacol ester

生成物 1

HCID 58447956Ethyl 2-(4-(2-methylpyridin-4-yl)phenyl)acetate

試薬・触媒・溶媒 2

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

反応条件

温度
90 °C

実験手順

To a sealed tube were added 2-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (2.2 g, 10 mmol), ethyl 2-(4-iodophenyl)acetate 26-1 (2.9 g, 10 mmol), Pd(PPh3)4 (0.231 g, 0.2 mmol), toluene (30 mL), ethanol (10 mL) and 2M Na2CO3 (10 mL). The reaction mixture was flushed with nitrogen and stirred at 90° C. for 10 hours. After cooled down to room temperature, the reaction mixture was diluted into 200 mL ethyl acetate and washed with saturated sodium bicarbonate solution and then brine. The organic phase was dried over Na2SO4 and then taken to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 50% ethyl acetate in hexane to give ethyl 2-(4-(2-methylpyridin-4-yl)phenyl)acetate 26-2 as an oil. MS m/z 256.1 (M+1).

後処理

  1. customThe reaction mixture was flushed with nitrogen
  2. temperatureAfter cooled down to room temperature
  3. additionthe reaction mixture was diluted into 200 mL ethyl acetate
  4. washwashed with saturated sodium bicarbonate solution
  5. dry with materialThe organic phase was dried over Na2SO4
  6. customtaken to dryness by rotary evaporation
  7. customThe crude product was purified by silica gel flash chromatography
  8. washeluted with 50% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-12ecdbc9d793437094f0f3e0fb79a32f
出典データセット
uspto-grants-2016_01
特許番号
US09238646B2

関連ノート

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