5-Methoxy-3-pyridinecarboxaldehyde → HCID 68053719、化合物

HRID 1048938ノート

反応式

HRID 1048938 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=O)[CH:6]=[N:7][CH:8]=1.[F:11][C:12]1[CH:13]=[C:14]([NH:19][CH3:20])[C:15]([NH2:18])=[CH:16][CH:17]=1>CN(C=O)C.O.C(OCC)(=O)C>[F:11][C:12]1[CH:17]=[CH:16][C:15]2[N:18]=[C:9]([C:5]3[CH:6]=[N:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:19]([CH3:20])[C:14]=2[CH:13]=1

参加物

6

反応物 2

HCID 109755495-Methoxy-3-pyridinecarboxaldehydeHCID 184572835-Fluoro-N1-methylbenzene-1,2-diamine

生成物 1

HCID 68053719HCID 68053719、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

To a solution of 5-methoxypyridine-3-carbaldehyde (0.052 g, 0.378 mmol) in DMF (1.89 mL) were added the title compound from Example 1 Step B (0.053 g, 0.38 mmol) and Na2S2O5 (0.288 g, 1.51 mmol). The resulting mixture was stirred at 120° C. overnight, then cooled to room temperature and diluted with water and ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash chromatography on silica gel (50% ethyl acetate in hexanes, then 100% ethyl acetate) provided the title compound: LCMS m/z 258.17 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.56 (d, J=1.6 Hz, 1 H), 8.46 (d, J=2.9 Hz, 1 H), 7.66 (dd, J=8.6, 4.8 Hz, 1 H), 7.65 (t, J=2.1, 2.1 Hz, 1 H), 7.12-7.06 (m, 2 H), 3.95 (s, 3 H), 3.88 (s, 3 H).

後処理

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel (50% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-f72b5d97ba9245de8e13dbd2f23445c0
出典データセット
uspto-grants-2016_07
特許番号
US09382226B2

反応ノート

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