Hydrochloric Acid → 8-Chloro-5-(3-fluorophenyl)imidazo[1,2-a]pyridine-6-carboxylic acid

HRID 717830ノート

反応式

HRID 717830 の反応式
[Cl:1][C:2]1[C:3]2[N:4]([CH:19]=[CH:20][N:21]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([C:8]([O:10]C)=[O:9])[CH:7]=1.[OH-].[Na+].O.Cl>O1CCCC1>[Cl:1][C:2]1[C:3]2[N:4]([CH:19]=[CH:20][N:21]=2)[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([C:8]([OH:10])=[O:9])[CH:7]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962Water2 回HCID 14798Sodium HydroxideHCID 58515952Methyl 8-chloro-5-(3-fluorophenyl)imidazo[1,2-a]pyridine-6-carboxylate

生成物 1

HCID 669927768-Chloro-5-(3-fluorophenyl)imidazo[1,2-a]pyridine-6-carboxylic acid収率 102.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
20 °C

実験手順

A solution of methyl 8-chloro-5-(3-fluorophenyl)imidazo[1,2-a]pyridine-6-carboxylate (0.18 g, 0.57 mmol) in tetrahydrofuran (3 mL) was treated with 1 M sodium hydroxide in water (1.7 mL, 1.7 mmol) and stirred at 20° C. for 6 hours. The reaction mixture was concentrated, diluted with water, cooled to 0° C., and treated with 1 M hydrogen chloride in water (2.3 mL, 2.3 mmol) dropwise. The resultant suspension was filtered to give the desired product (0.17 g, quantitative) that was used without further purification. LCMS calculated for C14H9ClFN2O2 (M+H)+: m/z=291.0. found: 290.9.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with water
  3. temperaturecooled to 0° C.
  4. filtrationThe resultant suspension was filtered

出典と根拠

ORDレコード
ord-91f554a5b32149e3960b2d0f3b75430b
出典データセット
uspto-grants-2015_11
特許番号
US09193721B2

反応ノート

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