Sodium Carbonate → 2-(2'-Chlorobiphenyl-4-yl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-phenyl}propanenitrile

HRID 2194892노트

반응식

HRID 2194892 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][O:21][C:22]3[C:27]([Cl:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[Cl:30])=[CH:14][CH:13]=2)[C:9]#[N:10])=[C:4](F)[CH:3]=1.[Cl:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>C(O)(C)(C)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1[C:2]1[CH:3]=[CH:4][C:5]([CH:8]([CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH2:19][CH2:20][O:21][C:22]3[C:23]([Cl:30])=[CH:24][C:25]([CH3:29])=[CH:26][C:27]=3[Cl:28])=[CH:16][CH:17]=2)[C:9]#[N:10])=[CH:6][CH:7]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 27343222-Chlorophenylboronic acidHCID 674456952-(4-Bromo-2-fluorophenyl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-phenyl}propanenitrile

생성물 1

HCID 674482422-(2'-Chlorobiphenyl-4-yl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]-phenyl}propanenitrile

시약·촉매·용매 3

HCID 11554889palladium acetate PPh3촉매HCID 962Water용매HCID 6386tert-Butanol용매

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온도
80 °C

실험 절차

To a solution 2-(4-bromo-2-fluorophenyl)-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propanenitrile (1 eq.) from step 1 and 2-chlorophenylboronic acid (2 eq.) in tert-butanol (0.16M) at room temperature was added palladium acetate/triphenyl phosphine (1:3; 0.05 eq.) and aqueous Na2CO3 (2M; 4 eq.). The mixture was stirred at 80° C. for 12 h, cooled to room temperature, poured in water and extracted with EtOAc. The organic extract was washed with brine, dried over MgSO4 filtered and concentrated. Purification by column chromatography on silica gel, eluting with Hex/Tol (55 to 65%) afforded the desired compound.

후처리

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. washwas washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography on silica gel
  9. washeluting with Hex/Tol (55 to 65%)

출처 및 근거

ORD 기록
ord-9198a90220414503a96d6151b1a536fc
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334308B2

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