Hydrochloric Acid → 3-(5-Fluoro-pyridin-2-yl)-isoxazole-4-carboxylic acid ethyl ester

HRID 83463

반응식

HRID 83463 반응식
ClN1C(=O)CCC1=O.[F:9][C:10]1[CH:11]=[CH:12][C:13]([CH:16]=[N:17][OH:18])=[N:14][CH:15]=1.CN([CH:22]=[CH:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])C.C(N(CC)CC)C.Cl>CN(C=O)C.C(Cl)(Cl)Cl>[CH2:27]([O:26][C:24]([C:23]1[C:16]([C:13]2[CH:12]=[CH:11][C:10]([F:9])=[CH:15][N:14]=2)=[N:17][O:18][CH:22]=1)=[O:25])[CH3:28]

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 121015Ethyl 3-(N,N-dimethylamino)acrylateHCID 1363872515-Fluoro-pyridine-2-carbaldehyde oxime

생성물 1

HCID 666436143-(5-Fluoro-pyridin-2-yl)-isoxazole-4-carboxylic acid ethyl ester수율 72%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a solution of N-chlorosuccinimide (17.34 g, 130 mmol) in DMF (128 mL) was added 5-fluoro-pyridine-2-carbaldehyde oxime (18.2 g, 130 mmol) portionwise over 2 h at room temperature and as the reaction warmed up to 60° C. the mixture was cooled back to room temperature with an ice-water bath and the resulting mixture was then stirred for 64 h at room temperature. To this solution was then added ethyl 3-(N,N-dimethylamino)acrylate (18.6 g, 130 mmol) and triethylamine (36.2 mL, 260 mmol) in chloroform (64 mL) and the resulting mixture was then stirred for 1 h at room temperature and poured onto a mixture of ice water and HCl (4 N, 1 L) and extracted with ethylacetate. The organic extract was then washed with water, saturated aqueous sodium hydrogen carbonate solution, brine, dried with sodium sulfate, filtered and evaporated. Purification by chromatography (SiO2, heptane:ethylacetate=100:0 to 1:1) afforded the title product (21.96 g, 72%) which was obtained as a yellow solid. MS: m/e=237.1 [M+H]+.

후처리

  1. temperaturewas cooled back to room temperature with an ice-water bath
  2. extractionextracted with ethylacetate
  3. extractionThe organic extract
  4. washwas then washed with water, saturated aqueous sodium hydrogen carbonate solution, brine
  5. dry with materialdried with sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by chromatography (SiO2, heptane:ethylacetate=100:0 to 1:1)

출처 및 근거

ORD 기록
ord-2681dd3e508647f09aa662550c4cca41
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846719B2

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