Dimethylformamide → (2-Chloro-6-cyano-naphthalen-1-yl)-acetic acid ethyl ester

HRID 639200노트

반응식

HRID 639200 반응식
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][C:12](OS(C(F)(F)F)(=O)=O)=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[Cl:24])[CH3:2].[CH3:26][N:27](C=O)C>C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd].[C-]#N.[Zn+2].[C-]#N>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([C:26]#[N:27])=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[Cl:24])[CH3:2]

참가 물질

5

반응물 2

HCID 6228DimethylformamideHCID 86623398(2-Chloro-6-trifluoromethanesulfonyloxy-naphthalen-1-yl)-acetic acid ethyl ester

생성물 1

HCID 68704275(2-Chloro-6-cyano-naphthalen-1-yl)-acetic acid ethyl ester

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매

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온도
125 °C

실험 절차

(2-Chloro-6-trifluoromethanesulfonyloxy-naphthalen-1-yl)-acetic acid ethyl ester (3.59 g, 9.04 mmol) is dissolved in DMF (30 ml) under an atmosphere of argon. After addition of palladium(0) tetrakis(triphenylphosphane) (418 mg, 0.36 mmol) and zinc(II) cyanide (2.12 g, 18.09 mmol), the reaction mixture is heated to 125° C. After 1 h, TLC analysis indicates complete consumption of starting material. The suspension is cooled to RT and poured onto water. Extraction with EtOAc is followed by washing the organic layer with 1 M aqueous HCl, sat. aqueous NaHCO3 solution and brine. After drying over Na2SO4 and removal of solvent, purification by FCC (hexane/EtOAc 3:1) affords the title compound. 1H NMR (d6-DMSO, 400 MHz): δ 1.06 (t, J=8 Hz, 3H), 3.98 (q, J=8 Hz, 2H), 4.24 (s, 2H), 7.66 (d, J=10 Hz, 1H), 7.79 (d, J=10 Hz, 1H), 7.96 (d, J=10 Hz, 1H), 8.13 (d, J=10 Hz, 1H), 8.54 (s, 1H).

후처리

  1. customconsumption of starting material
  2. temperatureThe suspension is cooled to RT
  3. additionpoured onto water
  4. extractionExtraction with EtOAc
  5. washby washing the organic layer with 1 M aqueous HCl, sat. aqueous NaHCO3 solution and brine
  6. dry with materialAfter drying over Na2SO4 and removal of solvent, purification by FCC (hexane/EtOAc 3:1)

출처 및 근거

ORD 기록
ord-d0ee6f39e8a54df08c987918d63e38b7
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691861B2

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