Potassium Carbonate → 5-(5-Bromopyridin-2-yl)-4-ethyloxazole

HRID 1672574ノート

反応式

HRID 1672574 の反応式
[N+:1]([CH:3](S(C1C=CC(C)=CC=1)(=O)=O)[CH2:4][CH3:5])#[C-:2].[Br:16][C:17]1[CH:18]=[CH:19][C:20]([CH:23]=[O:24])=[N:21][CH:22]=1.C([O-])([O-])=O.[K+].[K+]>CO>[Br:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[O:24][CH:2]=[N:1][C:3]=2[CH2:4][CH3:5])=[N:21][CH:22]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 98775625-Bromopyridine-2-carbaldehydeHCID 204671891-Ethyl-1-tosylmethyl isocyanide

生成物 1

HCID 666965965-(5-Bromopyridin-2-yl)-4-ethyloxazole収率 88%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 1-(1-isocyanopropylsulfonyl)-4-methylbenzene (1.98 g, 8.87 mmol), 5-bromopicolinaldehyde (1.65 g, 8.87 mmol), and K2CO3 (1.47 g, 10.6 mmol) in MeOH (45 mL) was heated at reflux overnight. The reaction was cooled to ambient temperature and concentrated in vacuo. Water was added to the residue and the product was extracted with EtOAc. The combined organic extract was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was chromatographed on silica gel (Analogix® 25×60 column, 10%-50% EtOAc/hexanes) to yield 1.97 g (88%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 8.68 (dd, J=2.4, 0.5, 1H), 7.89-7.82 (m, 2H), 7.55-7.49 (m, 1H), 3.06 (q, J=7.5, 2H), 1.29 (t, J=7.5, 3H). MS (DCI+) m/z 253/255 (M+H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated in vacuo
  4. additionWater was added to the residue
  5. extractionthe product was extracted with EtOAc
  6. extractionThe combined organic extract
  7. washwas washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe crude product was chromatographed on silica gel (Analogix® 25×60 column, 10%-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-ee852080ca7f4a08b4c52efa68c8e990
出典データセット
uspto-grants-2011_08
特許番号
US07998993B2

反応ノート

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