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

HRID 592155

반응식

HRID 592155 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-2cab6c97868a4e3b91a2c368f2fa615c
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238646B2

연결된 노트

불러오는 중…