Sodium Carbonate → Methyl 5-(pyridin-4-yl)thiophene-2-carboxylate

HRID 278554

反応式

HRID 278554 の反応式
Br[C:2]1[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=1.[N:11]1[CH:16]=[CH:15][C:14](OB(O)O)=[CH:13][CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.C(OCC)(=O)C>[N:11]1[CH:16]=[CH:15][C:14]([C:2]2[S:6][C:5]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:3]=2)=[CH:13][CH:12]=1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 605713Methyl 5-bromothiophene-2-carboxylateHCID 218058124-Pyridylboric acid

生成物 1

HCID 21928559Methyl 5-(pyridin-4-yl)thiophene-2-carboxylate収率 54.2%

試薬・触媒・溶媒 2

HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of methyl 5-bromo-2-thiophenecarboxylate (884 mg), 4-pyridyl boric acid (500 mg), tetrakistriphenylphosphine palladium(0) (250 mg) in dimethoxyethane (15 ml) was added 2 M sodium carbonate solution (4 ml) and the solution was heated for 15 hours under reflux. The reaction solution was diluted with ethyl acetate and the organic layer was separated, washed with water and extracted with 1 N hydrochloric acid. The extract was made alkaline with sodium hydroxide solution and extracted with ethyl acetate. The extract was dried and concentrated to give pale yellow solid of methyl 5-(4-pyridyl)-2-thiophenecarboxylate (428 mg).

後処理

  1. temperaturethe solution was heated for 15 hours
  2. temperatureunder reflux
  3. customthe organic layer was separated
  4. washwashed with water
  5. extractionextracted with 1 N hydrochloric acid
  6. extractionextracted with ethyl acetate
  7. customThe extract was dried
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-ea864b6b5fcf42098a526fd3634311dd
出典データセット
uspto-grants-2002_03
特許番号
US06359134B1

関連ノート

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