2-Pyridinecarboxaldehyde → HCID 58808699, 화합물

HRID 1921547노트

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HRID 1921547 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 58808699HCID 58808699, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-3a962bad121345e0a9e9048a9ca2c49e
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173682B2

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