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

HRID 1672574노트

반응식

HRID 1672574 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ee852080ca7f4a08b4c52efa68c8e990
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07998993B2

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