Water → Ethyl 2-[4-chloro-2-fluoro-5-(1-methylethoxy)phenyl]octahydro-1-oxoimidazo[1,5-a]pyridine-3-carboxylate

HRID 263384ノート

反応式

HRID 263384 の反応式
C(=O)([O-])[O-].[K+].[K+].Br[CH:8](F)[C:9]([O:11][CH2:12][CH3:13])=[O:10].[Cl:15][C:16]1[C:21]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:20][C:19]([NH:26][C:27]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][NH:30]2)=[O:28])=[C:18]([F:35])[CH:17]=1.O>C(#N)C.C(OCC)(=O)C>[Cl:15][C:16]1[C:21]([O:22][CH:23]([CH3:25])[CH3:24])=[CH:20][C:19]([N:26]2[C:27](=[O:28])[CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][N:30]3[CH:8]2[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:18]([F:35])[CH:17]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2733407Acetic acid, 2-bromo-2-fluoro-, ethyl esterHCID 19037321N-[4-Chloro-2-fluoro-5-(1-methylethoxy)phenyl]piperidine-2-carboxamide

生成物 1

HCID 19037326Ethyl 2-[4-chloro-2-fluoro-5-(1-methylethoxy)phenyl]octahydro-1-oxoimidazo[1,5-a]pyridine-3-carboxylate収率 21.1%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of potassium carbonate (724 mg, 5.24 mmol), ethyl bromofluoroacetate (882 mg, 4.76 mmol) and the product of Step A (1.5 g, 4.76 mmol) in acetonitrile (50 mL) was heated at reflux overnight. 100 mL of H2O and 200 mL of ethyl acetate were added to the mixture. The organic layer was separated, dried (MgSO4), filtered, and evaporated under vacuum to dryness. Flash chromatography yielded the title compound of Step B as a white solid (400 mg) m.p. 83°-85° C. 1H NMR δ7.21 (d,1H), 7.18 (d,1H), 4.92 (s,1H), 4.50 (m,1H), 4.16-4.09 (m,2H), 3.29 (m,1H), 2.95 (m,1H), 2.50 (m,1H), 2.10 (m,1H), 1.96 (m,1H), 1.80-1.58 (m,2H), 1.37 (d,6H), 1.35 (t,3H).

後処理

  1. temperatureat reflux overnight
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated under vacuum to dryness

出典と根拠

ORDレコード
ord-9dc2de2cdd334059be8b20ecf8b907cd
出典データセット
uspto-grants-1997_07
特許番号
US05643855

反応ノート

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