Hydrochloric Acid → 6-(4-Fluorophenyl)nicotinic acid

HRID 915645ノート

反応式

HRID 915645 の反応式
C[O:2][C:3]([C:5]1[CH:6]=[N:7][C:8]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:9][CH:10]=1)=[O:4].[OH-].[Na+].Cl>O1CCCC1>[F:17][C:14]1[CH:15]=[CH:16][C:11]([C:8]2[N:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:10][CH:9]=2)=[CH:12][CH:13]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 110317126-(4-Fluorophenyl)pyridine-3-carboxylic acid methyl ester

生成物 1

HCID 227301866-(4-Fluorophenyl)nicotinic acid収率 37%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Combine 6-bromopyridine-3-carboxylic acid methyl ester (1.03 g, 4.78 mmol), 4-fluorophenylboronic acid (1.88 g, 13.41 mmol), and cesium fluoride (2.55 g, 16.78 mmol) in dimethylformamide (25 mL) and water (4 mL) with stirring. Place the hetereogeneous reaction mixture, open to the air, in an oil bath maintained at 80° C. After 5 minutes of heating, add Pd(OAc)2 (150 mg, 0.67 mmol) in one portion. After 17 hours, cool the reaction to room temperature, dilute with ethyl acetate and filter through a short plug of celite with additional ethyl acetate. Wash the organics with water, dry over magnesium sulfate, filter and evaporate. Purification by flash column chromatography yields 6-(4-fluorophenyl)pyridine-3-carboxylic acid methyl ester as a yellow solid. Dissolve the purified ester in tetrahydrofuran (0.25M) and add an equal volume of 1M sodium hydroxide. Stir vigorously at room temperature for 15 hours. Upon completion, acidify the reaction with conc. HCl and collect the white precipitate by filtration. Drying under vacuum yields 385 mg (37%) of the title compound. MS (m/e): 218.1 (MH+)

後処理

  1. customcollect the white precipitate
  2. filtrationby filtration
  3. customDrying under vacuum

出典と根拠

ORDレコード
ord-b8cdfeb52b11472289bb9451a9088714
出典データセット
uspto-grants-2007_09
特許番号
US07265246B2

反応ノート

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