Sodium Carbonate → 2-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethanol

HRID 1916710노트

반응식

HRID 1916710 반응식
C([O-])([O-])=O.[Na+].[Na+].Br[C:8]1[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[N:21]([CH2:25][CH2:26][OH:27])[CH:20]=[CH:19]3)=[N:12][CH:13]=1.[Cl:28][C:29]1[CH:34]=[CH:33][C:32](OB(O)O)=[CH:31][CH:30]=1>O1CCOCC1.CO>[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([C:8]2[CH:9]=[CH:10][C:11]([C:14]#[C:15][C:16]3[CH:17]=[C:18]4[C:22](=[CH:23][CH:24]=3)[N:21]([CH2:25][CH2:26][OH:27])[CH:20]=[CH:19]4)=[N:12][CH:13]=2)=[CH:31][CH:30]=1

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 17810664p-Chlorophenylboric acidHCID 673628532-[5-(5-Bromo-pyridin-2-ylethynyl)-indol-1-yl]-ethanol

생성물 1

HCID 673637692-{5-[5-(4-Chloro-phenyl)-pyridin-2-ylethynyl]-indol-1-yl}-ethanol

시약·촉매·용매 2

HCID 887Methanol용매HCID 312751,4-Dioxane용매

반응 조건

온도
110 °C

실험 절차

Under an N2 atmosphere 56 mL 2 M Na2CO3 solution and 1.29 g (1.1 mmol) tetrakis-triphenylphosphane-palladium are added to a solution of 19.0 g (55.7 mmol) 2-[5-(5-bromo-pyridin-2-ylethynyl)-indol-1-yl]-ethanol and 11.55 g (72.4 mmol) 4-chlorophenyl-boric acid in 320 mL 1,4-dioxane and 80 mL MeOH and the reaction mixture is heated to 110° C. for 16 h. The mixture is evaporated down i. vac., the residue is combined with 300 mL water and the suspension is stirred vigorously. The precipitate is filtered off and washed with 200 mL water. The precipitate is suspended three times, each time with 600 mL PE/DCM (5:1), suction filtered and finally dried in the air until a constant weight is obtained.

후처리

  1. customThe mixture is evaporated down i
  2. filtrationThe precipitate is filtered off
  3. washwashed with 200 mL water
  4. filtrationeach time with 600 mL PE/DCM (5:1), suction filtered
  5. customfinally dried in the air until a constant weight
  6. customis obtained

출처 및 근거

ORD 기록
ord-9ea2b469ed1b4fe1a1b90051c789402f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618132B2

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