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

HRID 717830노트

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HRID 717830 반응식
[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

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962Water2회HCID 14798Sodium HydroxideHCID 58515952Methyl 8-chloro-5-(3-fluorophenyl)imidazo[1,2-a]pyridine-6-carboxylate

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
20 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-91f554a5b32149e3960b2d0f3b75430b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193721B2

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