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

HRID 1046015

反応式

HRID 1046015 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5b21c090da10449881c1e6e5cd981550
出典データセット
uspto-grants-2013_10
特許番号
US08569319B2

関連ノート

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