Potassium Carbonate → N-(2,4-dimethoxybenzyl)-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine

HRID 595931ノート

反応式

HRID 595931 の反応式
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:14])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][N:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[CH2:25][NH2:26].CCN(C(C)C)C(C)C.C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[CH3:15][O:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[CH2:25][NH:26][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH3:14])[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)=[CH:4][N:3]=1

参加物

6

反応物 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 5972502,4-DimethoxybenzylamineHCID 1180455832-fluoro-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridine

生成物 1

HCID 118045285N-(2,4-dimethoxybenzyl)-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine収率 51.8%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
160 °C

実験手順

To a solution of 2-fluoro-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridine (110 mg, 0.56 mmol) in (2,4-dimethoxyphenyl)methanamine (1016 μL, 6.76 mmol) and DIEA (246 μL, 1.41 mmol) was added potassium carbonate (156 mg, 1.12 mmol). The resulting mixture was heated to 160° C. in an oil bath for 16 h, The reaction mixture was diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified by flash column chromatography on silicagel (ISCO) eluting with 0-100% ethyl acetate in heptane to give N-(2,4-dimethoxybenzyl)-5-(4-methyltetrahydro-2H-pyran-4-yl)pyridin-2-amine (100 mg, 0.29 mmol, 51.8% yield) as light yellow color solid. LCMS (m/z): 343 (MH+), 0.63 min.

後処理

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography on silicagel (ISCO)
  5. washeluting with 0-100% ethyl acetate in heptane

出典と根拠

ORDレコード
ord-733b9243744140e4b7752ba245f56bff
出典データセット
uspto-grants-2016_01
特許番号
US09242996B2

反応ノート

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