Sodium Bicarbonate → 2-[1-methyl-1-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)-2-(tetrahydro-2H-pyran-4-yl)ethyl]-5-(methylsulfanyl)pyridine

HRID 1882122ノート

反応式

HRID 1882122 の反応式
[CH3:1][C:2]([C:22]1[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][N:23]=1)([CH2:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)[C:3](=O)[CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=O.C([O-])(=O)C.[NH4+:34].C(=O)([O-])O.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[CH3:1][C:2]([C:22]1[CH:27]=[CH:26][C:25]([S:28][CH3:29])=[CH:24][N:23]=1)([C:3]1[NH:34][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)=[CH:5][CH:4]=1)[CH2:15][CH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 593314515-methyl-5-[5-(methylsulfanyl)pyridin-2-yl]-1-(pyridin-2-yl)-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

生成物 1

HCID 593312412-[1-methyl-1-(5-(pyridin-2-yl)-1H-pyrrol-2-yl)-2-(tetrahydro-2H-pyran-4-yl)ethyl]-5-(methylsulfanyl)pyridine収率 145.1%

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

To a solution of 5-methyl-5-[5-(methylsulfanyl)pyridin-2-yl]-1-(pyridin-2-yl)-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (60.7 mg) in acetic acid (1 mL) was added ammonium acetate (181 mg), and the mixture was stirred at 110° C. for 1 hr. After cooling to room temperature, the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution. The reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (84.0 mg, yield 82%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio).

後処理

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. dry with materialThe ethyl acetate layer was dried (MgSO4)
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-9df2e48b43b74192ab914f12c22df32a
出典データセット
uspto-grants-2012_11
特許番号
US08318746B2

反応ノート

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