Ethyl Acetate → N-(4-cyano-2-fluoro-5-(trifluoromethyl)phenyl)acetamide

HRID 1504944ノート

反応式

HRID 1504944 の反応式
Br[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([NH:12][C:13](=[O:15])[CH3:14])=[C:4]([F:16])[CH:3]=1.[C:17]([Cu])#[N:18].CCOC(C)=O>CN(C=O)C>[C:17]([C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5]([NH:12][C:13](=[O:15])[CH3:14])=[C:4]([F:16])[CH:3]=1)#[N:18]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 23274446N-[4-Bromo-2-fluoro-5-(trifluoromethyl)phenyl]acetamideHCID 178418546HCID 178418546、化合物

生成物 1

HCID 68292028N-(4-cyano-2-fluoro-5-(trifluoromethyl)phenyl)acetamide収率 56.9%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
150 °C

実験手順

A mixture of compound 23 (300 mg, 1 mmol), CuCN (355 mg, 4 mmol) in DMF (6 mL) was heated at 150° C. under N2 overnight. The reaction mixture was cooled to room temperature and then poured into ice water. EtOAc was added and the insoluble solid was filtered off (rinsed with EtOAc). The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with aq.NaHCO3 and brine, dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified with silica gel chromatography (PE:EtOAc=4:1) to afford the title compound 24 (140 mg, 28%) as a white solid. 1H NMR (400 MHz, CDCl3) δ8.99 (d, 1H, J=7.2 Hz), 7.55 (d, 1H, J=10.0 Hz), 2.92 (s, 3H).

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe insoluble solid was filtered off
  3. wash(rinsed with EtOAc)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with EtOAc
  6. washThe combined organic layers were washed with aq
  7. dry with materialNaHCO3 and brine, dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified with silica gel chromatography (PE:EtOAc=4:1)

出典と根拠

ORDレコード
ord-fde8eaaa87d243409581d7a5eada02e4
出典データセット
uspto-grants-2015_12
特許番号
US09216957B2

反応ノート

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