Water → Methyl 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

HRID 1046015

반응식

HRID 1046015 반응식
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[O:9]=[C:10]1[C:15]([C:16]([O:18][CH3:19])=[O:17])=[CH:14][CH:13]=[CH:12]O1.Cl.CN(C)CCCN=C=NCC.O>CN(C=O)C.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:8]=[CH:7][C:5]([N:6]2[CH:12]=[CH:13][CH:14]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[C:10]2=[O:9])=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 97314-FluoroanilineHCID 117704Methyl 2-oxo-2H-pyran-3-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 1

HCID 21081723Methyl 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-fluoroaniline (6.5 g, 58.4 mmol) in DMF (30 mL) at ice bath temperature was added methyl 2-oxo-2H-pyran-3-carboxylate (9.0 g, 58.4 mmol). The resulting mixture was stirred for 15 min cold and was then warmed to ambient temp for 3 hours. N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI—HCl) (13.5 g, 70.0 mmol) and DMAP (1.43 g, 11.7 mmol) were added and the resulting mixture was stirred at ambient temp overnight. The reaction mixture was poured into water (300 mL), extracted with ethyl acetate (3×100 mL), washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to obtain methyl 1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxylate. This crude product was used for the next step without further purification.

후처리

  1. stirringthe resulting mixture was stirred at ambient temp overnight
  2. extractionextracted with ethyl acetate (3×100 mL)
  3. washwashed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-5b21c090da10449881c1e6e5cd981550
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569319B2

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