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

HRID 1470432노트

반응식

HRID 1470432 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-bd64d73e1f6045cf807d8f3a0c81d51b
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006446B2

반응 노트

불러오는 중…