Dimethylformamide → Ethyl 2-(5-amino-2-cyano-4-fluorophenyl)acetate

HRID 1257244노트

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HRID 1257244 반응식
[NH2:1][C:2]1[C:3]([F:15])=[CH:4][C:5](Br)=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=1.[CH3:16][N:17](C=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>[NH2:1][C:2]1[C:3]([F:15])=[CH:4][C:5]([C:16]#[N:17])=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:7]=1

참가 물질

4

반응물 2

HCID 6228DimethylformamideHCID 86713632HCID 86713632, 화합물

생성물 1

HCID 68982767Ethyl 2-(5-amino-2-cyano-4-fluorophenyl)acetate수율 25%

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

반응 조건

온도
100 °C

실험 절차

A solution of Example C5 (3 g, 10.9 mmol) in DMF (50 mL) was treated with ZnCN2 (1.7 g, 16.4 mmol) and Pd(PPh3)4 (1.26 g, 1.09 mmol), sparged with N2 and heated at 100° C. for 12 h. The mixture was cooled to RT, treated with water and extracted with EtOAc (3×). The combined organics were washed with brine (3×), dried over Na2SO4, concentrated to dryness and purified via silica gel chromatography (EtOAc/pet ether) to afford ethyl 2-(5-amino-2-cyano-4-fluorophenyl)acetate (600 mg, 25% yield). 1H NMR (400 MHz, CDCl3): δ 7.19 (d, J=2.4 Hz, 1H), 6.67 (d, J=8.4 Hz, 1H), 4.13-4.11 (q, J=6.8 Hz, 2H), 3.66 (s, 2H), 1.23-1.19 (t, J=6.8 Hz, 3H).

후처리

  1. customsparged with N2
  2. temperatureThe mixture was cooled to RT
  3. additiontreated with water
  4. extractionextracted with EtOAc (3×)
  5. washThe combined organics were washed with brine (3×)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness
  8. custompurified via silica gel chromatography (EtOAc/pet ether)

출처 및 근거

ORD 기록
ord-b3af355249e345a2b718928e1461f443
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461179B1

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