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

HRID 2194892ノート

反応式

HRID 2194892 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11554889palladium acetate PPh3触媒HCID 962Water溶媒HCID 6386tert-Butanol溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-9198a90220414503a96d6151b1a536fc
出典データセット
uspto-grants-2012_12
特許番号
US08334308B2

反応ノート

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