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

HRID 1269632ノート

反応式

HRID 1269632 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒2 回HCID 80711,2-Dimethoxyethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-95d5904f7e594812983978ced455bd3a
出典データセット
uspto-grants-2007_04
特許番号
US07199239B2

反応ノート

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