Sodium Carbonate → 2-Chloro-6-(4-(trifluoromethyl)phenyl)pyrazine

HRID 1269632노트

반응식

HRID 1269632 반응식
Cl[C:2]1[CH:7]=[N:6][CH:5]=[C:4]([Cl:8])[N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[F:15][C:16]([F:27])([F:26])[C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1>C(COC)OC.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:8][C:4]1[CH:5]=[N:6][CH:7]=[C:2]([C:20]2[CH:21]=[CH:22][C:17]([C:16]([F:27])([F:26])[F:15])=[CH:18][CH:19]=2)[N:3]=1

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 785042,6-DichloropyrazineHCID 27343894-(Trifluoromethyl)phenylboronic acid

생성물 1

HCID 184483272-Chloro-6-(4-(trifluoromethyl)phenyl)pyrazine수율 36.5%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

실험 절차

To a mixture of 2,6-dichloropyrazine (0.5 g, 3.36 mmol), sodium carbonate (0.925 g, 8.73 mmol) and 4-trifluoromethylphenylboronic acid (0.638 g, 3.36 mmol) in dimethoxyethane (15 mL) and water (7.5 mL) under nitrogen was added tetrakis(triphenylphosphine) palladium (0) (0.078 g). The resulting mixture was heated at reflux for 5 h under nitrogen, before stirring at room temperature overnight. The reaction was diluted with water (50 mL) and extracted with chloroform (2×75 mL). The organic solution was dried (MgSO4) and the solvents removed in vacuo. Purification by Biotage™ chromatography (Silica, 90 g) 10:1–6:1 cyclohexane:EtOAc afforded the title compound as a white solid (0.317 g).

후처리

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 5 h under nitrogen
  3. extractionextracted with chloroform (2×75 mL)
  4. dry with materialThe organic solution was dried (MgSO4)
  5. customthe solvents removed in vacuo
  6. customPurification by Biotage™ chromatography (Silica, 90 g) 10:1–6:1 cyclohexane

출처 및 근거

ORD 기록
ord-95d5904f7e594812983978ced455bd3a
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199239B2

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