Sodium Bicarbonate → 2-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethanol

HRID 734790노트

반응식

HRID 734790 반응식
C(=O)(O)[O-].[Na+].Br[C:7]1[CH:8]=[CH:9][C:10]([C:13]#[C:14][C:15]2[CH:24]=[CH:23][C:18]([O:19][CH2:20][CH2:21][OH:22])=[C:17]([CH3:25])[CH:16]=2)=[N:11][CH:12]=1.[Cl:26][C:27]1[CH:32]=[CH:31][C:30](OB(O)O)=[CH:29][CH:28]=1>O1CCOCC1>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([C:7]2[CH:8]=[CH:9][C:10]([C:13]#[C:14][C:15]3[CH:24]=[CH:23][C:18]([O:19][CH2:20][CH2:21][OH:22])=[C:17]([CH3:25])[CH:16]=3)=[N:11][CH:12]=2)=[CH:29][CH:28]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 17810664p-Chlorophenylboric acid2회HCID 690586072-[4-(5-Bromopyridin-2-ylethynyl)-2-methylphenoxy]ethanol

생성물 1

HCID 673624362-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethanol

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

40 mL of 2 N aqueous sodium bicarbonate solution was added to a suspension of 13.20 g (39.74 mmol) of 2-[4-(5-bromopyridin-2-ylethynyl)-2-methylphenoxy]ethanol, 9.32 g (59.60 mmol) of 4-chlorophenylboric acid, and 2.30 g (1.99 mmol) of tetrakis(triphenylphosphane)palladium in 400 mL of 1,4-dioxane and the mixture was refluxed for 12 hours. Another 4.66 g of 4-chlorophenylboric acid and 1.14 g of tetrakis(triphenylphosphane)palladium were added and the mixture was refluxed for 8 hours. The reaction mixture was evaporated down in vacuo and the residue was stirred with EtOAc and water. The precipitate was filtered off, washed with diethyl ether, and dried in vacuo. Yield: 10.70 g (74% of theoretical); C22H18ClNO2 (M=363.837); calc.: molpeak (M+H)+: 364/366 (Cl); found: molpeak (M+H)+: 364/366 (Cl); Rf value: 0.47 (silica gel, DCM/EtOAc 2:1).

후처리

  1. temperaturethe mixture was refluxed for 12 hours
  2. temperaturethe mixture was refluxed for 8 hours
  3. customThe reaction mixture was evaporated down in vacuo
  4. filtrationThe precipitate was filtered off
  5. washwashed with diethyl ether
  6. customdried in vacuo

출처 및 근거

ORD 기록
ord-71883cc4b6dc4e3096aaa7a0c013533f
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592358B2

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