Cesium fluoride → 2-[2'-(3-Methoxypropyl)-3-methylbiphenyl-4-yl]-3-pyridin-3-ylpropanenitrile

HRID 2194921노트

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HRID 2194921 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[C:9]#[N:10])=[C:4]([CH3:18])[CH:3]=1.[CH3:19][O:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1B(O)O.[F-].[Cs+]>COCCOC.O>[CH3:19][O:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[C:9]#[N:10])=[C:4]([CH3:18])[CH:3]=1

참가 물질

6

반응물 3

HCID 25953Cesium fluorideHCID 58083347[2-(3-Methoxypropyl)phenyl]boronic acidHCID 674455322-(4-Bromo-2-methylphenyl)-3-pyridin-3-ylpropanenitrile

생성물 1

HCID 674474272-[2'-(3-Methoxypropyl)-3-methylbiphenyl-4-yl]-3-pyridin-3-ylpropanenitrile

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a solution 2-(4-bromo-2-methylphenyl)-3-pyridin-3-ylpropanenitrile (1 eq.) from step 1 and [2-(3-methoxypropyl)phenyl]boronic acid from EXAMPLE 3, step 1 (1.2 eq.) in DME (0.1M) at room temperature was added palladium tetrakistriphenyl phosphine (Pd(PPh3)4; 0.05 eq.) and CsF (2.4 eq.). The mixture was refluxed for 2 h, cooled to room temperature, poured in water and extracted with EtOAc. The organic extract was washed with water, brine, dried over Na2SO4 filtered and concentrated. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (0 to 65% in 30 min) afforded the desired compound.

후처리

  1. temperatureThe mixture was refluxed for 2 h
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with water, brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
  9. washeluting with Hex/EtOAc (0 to 65% in 30 min)

출처 및 근거

ORD 기록
ord-56da723d34294edbb740bf37cf5679bd
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334308B2

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