2-Pyridinecarboxaldehyde → HCID 58808699、化合物

HRID 1921547ノート

反応式

HRID 1921547 の反応式
[CH2:1]([C:3]1[C:4](=[O:15])[NH:5][C:6]([CH3:14])=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2].[Li]CCCC.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH:27]=[O:28]>C1COCC1>[CH2:1]([C:3]1[C:4](=[O:15])[NH:5][C:6]([CH3:14])=[C:7]([C:9]2[S:10][C:11]([CH:27]([OH:28])[C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=3)=[CH:12][CH:13]=2)[CH:8]=1)[CH3:2]

参加物

5

反応物 3

HCID 142732-PyridinecarboxaldehydeHCID 674922683-ethyl-6-methyl-5-thiophen-2-yl-1H-pyridin-2-oneHCID 178418339Butyllithium

生成物 1

HCID 58808699HCID 58808699、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A solution of 3-ethyl-6-methyl-5-thiophen-2-yl-1H-pyridin-2-one prepared in accordance with the procedures of Example 24, Step 3 (97 mg, 0.442 mmol) in anhydrous THF (1 ml) is cooled to −78° C., and n-BuLi (2.5 M in hexane, 0.4 ml, 1 mmol) is added. The resulting dark green mixture is stirred for 30 min, and then pyridine-2-carbaldehyde (80 mg, 0.746 mmol) is added. The cooling bath is removed after 20 min, and the reaction mixture is slowly warmed to room temperature. After 3 hr, water (5 ml) is added to the mixture, and it is extracted with ethyl acetate. The organic phases are washed and dried, and the residue is purified on silica gel to afford a yellow solid (60 mg). MS: m/e=327 (M+H). 1H-NMR (D6-DMSO, δ ppm) 11.65 (s, 1H); 8.51 (d, 1H); 7.85 (d, 1H); 7.61 (d, 1H); 7.29 (m, 1H); 7.21 (s, 1H); 6.88 (m, 2H); 6.43 (d, 1H); 5.88 (d, 1H); 2.38 (q, 2H); 2.24 (s, 3H); 1.06 (t, 3H, J=7.4 Hz).

後処理

  1. customThe cooling bath is removed after 20 min
  2. temperaturethe reaction mixture is slowly warmed to room temperature
  3. waitAfter 3 hr
  4. additionwater (5 ml) is added to the mixture, and it
  5. extractionis extracted with ethyl acetate
  6. washThe organic phases are washed
  7. customdried
  8. customthe residue is purified on silica gel

出典と根拠

ORDレコード
ord-3a962bad121345e0a9e9048a9ca2c49e
出典データセット
uspto-grants-2012_05
特許番号
US08173682B2

反応ノート

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