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

HRID 595931노트

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HRID 595931 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
160 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-733b9243744140e4b7752ba245f56bff
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242996B2

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