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

HRID 533324ノート

反応式

HRID 533324 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-37d98f059fe948edb2fc48a0fa407da0
出典データセット
uspto-grants-2014_10
特許番号
US08853246B2

反応ノート

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