Thiophenol → HCID 66849112, 화합물

HRID 1034593노트

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HRID 1034593 반응식
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[NH2:10][C:11]1[C:16](Br)=[N:15][C:14]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:13][N:12]=1>CN(C=O)C>[NH2:10][C:11]1[C:16]([S:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[N:15][C:14]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)=[CH:13][N:12]=1

참가 물질

5

반응물 3

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 715237102-Amino-3-bromo-5-(4-methoxyphenyl)pyrazine

생성물 1

HCID 66849112HCID 66849112, 화합물수율 70%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
7.5 °C

실험 절차

To a cooled solution of thiophenol (0.08 mL, 0.7 mmol) in dry DMF (10 mL), sodium hydride (NaH) (0.025 g, 1.00 mmol) was added and the resulting mixture was stirred for 15 min at 5-10° C. After this time 2-amino-3-bromo-5-(4-methoxyphenyl)pyrazine 17a (0.20 g, 0.71 mmol) was added and the mixture refluxed for 6 h, cooled and extracted with EtOAc. The organic layer was washed with water, dried over Na2SO4, filtered and the solvent removed under reduced pressure to get a crude that was purified by flash chromatography using petroleum ether-EtOAc (65:45 v/v) as eluent, to obtain 0.15 g of the title compound 18a as an orange solid (mp 89-90° C., 70% yield). 1H-NMR (CDCl3): 3.81 (s, 3H), 4.90 (br s, 2H), 6.89 (d, J=8.7, 2H), 7.33-7.39 (m, 7.45-7.50 (m, 2H), 7.69 (d, J=8.7, 2H), 8.28 (s, 1H). MS (ESI): m/z 310 (M+H+).

후처리

  1. temperaturethe mixture refluxed for 6 h
  2. temperaturecooled
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure
  8. customto get a crude that
  9. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-7b74cafae9034ef3bff415d84327c0b2
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546147B2

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