Hydrochloric Acid → Cyclohexyl(3-methylfuro[3,2-b]pyridin-2-yl)methanone

HRID 2091207ノート

反応式

HRID 2091207 の反応式
[OH:1][C:2]1[C:3]([C:8](=O)[CH3:9])=[N:4][CH:5]=[CH:6][CH:7]=1.Br[CH2:12][C:13]([CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:14].C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH:15]1([C:13]([C:12]2[O:1][C:2]3[C:3](=[N:4][CH:5]=[CH:6][CH:7]=3)[C:8]=2[CH3:9])=[O:14])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 111600272-Bromo-1-cyclohexylethanoneHCID 140889471-(3-Hydroxypyridin-2-yl)ethan-1-one

生成物 1

HCID 66777549Cyclohexyl(3-methylfuro[3,2-b]pyridin-2-yl)methanone収率 53%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of 1-(3-hydroxypyridin-2-yl)ethanone (4.37 g), 2-bromo-1-cyclohexylethanone (9.82 g) synthesized in Example A51(1) and N,N-dimethylformamide (50 mL) was added potassium carbonate (13.2 g), and the mixture was stirred at room temperature for 2.5 days. 1N Hydrochloric acid was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (20% ethyl acetate/hexane) to give the title object compound (4.09 g, 53%) as a brown solid.

後処理

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (20% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-6c074e6de8944d27b331aba49216e674
出典データセット
uspto-grants-2013_05
特許番号
US08436043B2

反応ノート

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