Water → 1-(2-fluoro-4-nitrophenyl)-2,3-dihydro-1H-pyridin-4-one

HRID 2213359

反応式

HRID 2213359 の反応式
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:16][CH:15]=[C:14]([O:17][Si](C)(C)C)[CH2:13][CH2:12]1.C(=O)(OC)OCC=C.O>CS(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH:12]=[CH:13][C:14](=[O:17])[CH2:15][CH2:16]1

参加物

6

反応物 3

HCID 962WaterHCID 534788Methyl 2-propen-1-yl carbonateHCID 218781391-(2-Fluoro-4-nitrophenyl)-4-[(trimethylsilyl)oxy]-1,2,3,6-tetrahydropyridine

生成物 1

HCID 218776411-(2-fluoro-4-nitrophenyl)-2,3-dihydro-1H-pyridin-4-one収率 70.5%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 679Dimethyl Sulfoxide溶媒

実験手順

To a stirring solution of the enol silyl ether from step 2 (100.0 g, 322 mmol) and allyl methyl carbonate (43.6 g, 386 mmol) in DMSO (625 ml) at ambient temperature is added Pd(OAc)2 (7.20 g, 32 mmol). The resulting solution is stirred under N2 at ambient temperature overnight. H2O (1 liter) is added and solvent allowed to cool to ambient temperature. The aqueous layer is extracted with EtOAc (2×800 ml) and the organic layers combined, washed with brine (800 ml) and organics dried over MgSO4. The solvent is removed and residue recrystallized from EtOAc/MTBE to afford 53.6 g (70%) of the title compound as a yellow solid. 1H NMR (CDCl3) δ 2.71 (m, 2 H), 4.06 (m, 2 H), 5.41 (d, J=8 Hz, 1 H), 7.25 (m, 1 H), 7.35 (d, J=8 Hz, 1 H), 8.08 (m, 2 H); Anal. Calcd for C11H9FN2O3: C, 55.94; H, 3.84; N, 11.86; F, 8.04. Found: C, 55.82; H, 3.81; N, 11.67.

後処理

  1. temperatureto cool to ambient temperature
  2. extractionThe aqueous layer is extracted with EtOAc (2×800 ml)
  3. washwashed with brine (800 ml)
  4. dry with materialorganics dried over MgSO4
  5. customThe solvent is removed
  6. customresidue recrystallized from EtOAc/MTBE

出典と根拠

ORDレコード
ord-6b34ba62f4ab449ab2bc221aaa5af471
出典データセット
uspto-grants-2006_09
特許番号
US07105547B2

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