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

HRID 2199218ノート

反応式

HRID 2199218 の反応式
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]

参加物

5

反応物 3

HCID 962Water2 回HCID 33557Sodium AzideHCID 59580826Ethyl 5-bromo-2-(pyridin-3-yl)thiazole-4-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
75 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-92c0b4199aa74294b112ac2daaff31f2
出典データセット
uspto-grants-2016_06
特許番号
US09357780B2

反応ノート

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