Dimethylformamide → Tert-butyl 2-(3-cyano-4-(2-methylpyridin-4-yl)phenyl)acetate

HRID 592155

反応式

HRID 592155 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[C:16]#[N:17].[CH3:18][C:19]1[CH:24]=[C:23]([Sn](CCCC)(CCCC)CCCC)[CH:22]=[CH:21][N:20]=1.CN(C=O)C>C(OCC)(=O)C.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:16]([C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH:6]=[CH:7][C:2]=1[C:23]1[CH:22]=[CH:21][N:20]=[C:19]([CH3:18])[CH:24]=1)#[N:17]

参加物

6

反応物 3

HCID 6228DimethylformamideHCID 216605742-Methyl-4-(tributylstannyl)pyridineHCID 58447897Tert-butyl 2-(4-chloro-3-cyanophenyl)acetate

生成物 1

HCID 58447938Tert-butyl 2-(3-cyano-4-(2-methylpyridin-4-yl)phenyl)acetate

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

A mixture of tert-butyl 2-(4-chloro-3-cyanophenyl)acetate 111-7 (572 mg, 2.28 mmol), 2-methyl-4-(tributylstannyl)pyridine 111-8 (870 mg, 2.28 mmol) and Pd(PPh3)4 (220 mg, 0.2 mmol) and DMF (9 mL) was stirred at 120° C. for 10 hours under argon. After cooling to room temperature, the mixture was diluted with ethyl acetate, washed with saturated aqueous Na2S2O3 solution, water and brine, dried over Na2SO4, and concentrated to dryness by rotary evaporation. The crude was purified by silica gel flash chromatography, eluted with 5% methanol in dichloromethane to give tert-butyl 2-(3-cyano-4-(2-methylpyridin-4-yl)phenyl)acetate 111-9 as a yellow oil. MS m/z 309.2 (M+1).

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with saturated aqueous Na2S2O3 solution, water and brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated to dryness by rotary evaporation
  5. customThe crude was purified by silica gel flash chromatography
  6. washeluted with 5% methanol in dichloromethane

出典と根拠

ORDレコード
ord-2cab6c97868a4e3b91a2c368f2fa615c
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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