Water → Ethyl 5-amino-2-(pyridin-3-yl)thiazole-4-carboxylate

HRID 2199218노트

반응식

HRID 2199218 반응식
Br[C:2]1[S:6][C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].O.[N-:19]=[N+]=[N-].[Na+]>CN(C=O)C>[NH2:19][C:2]1[S:6][C:5]([C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

참가 물질

5

반응물 3

HCID 962Water2회HCID 33557Sodium AzideHCID 59580826Ethyl 5-bromo-2-(pyridin-3-yl)thiazole-4-carboxylate

생성물 1

HCID 59580498Ethyl 5-amino-2-(pyridin-3-yl)thiazole-4-carboxylate수율 30.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
75 °C

실험 절차

To a round bottom flask containing ethyl 5-bromo-2-(pyridin-3-yl)thiazole-4-carboxylate (2.5 g, 7.98 mmol) in DMF (26.6 ml)/water (13.3 ml) was carefully added sodium azide (2.59 g, 39.9 mmol) and stirred overnight at 75° C. The reaction was cooled to room temperature and poured into water which was extracted with ethyl acetate. The ethyl acetate layers were combined and washed with hexanes/water. The ethyl acetate extracts were dried (MgSO4), filtered and concentrated to dryness. The crude material was purified by silica gel column chromatography (0 to 75% ethylacetate/hexanes) to give the desired product as a white solid (0.6 g, 30%) 1H NMR (300 MHz, CDCl3) δ 8.98 (s, 1H), 8.63 (d, 1H), 8.19 (d, 1H), 7.45-7.32 (m, 1H), 6.3 (s, 2H), 4.46 (q, 2H), 1.43 (t, 3H). ESIMS m/z 251.1 (M+2).

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. extractionwas extracted with ethyl acetate
  3. washwashed with hexanes/water
  4. dry with materialThe ethyl acetate extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe crude material was purified by silica gel column chromatography (0 to 75% ethylacetate/hexanes)

출처 및 근거

ORD 기록
ord-92c0b4199aa74294b112ac2daaff31f2
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09357780B2

반응 노트

불러오는 중…