Potassium Carbonate → 1-(2-Azidoethyl)-3-methoxypyridine-2-one

HRID 539534노트

반응식

HRID 539534 반응식
[CH3:1][O:2][C:3]1[C:4](=[O:9])[NH:5][CH:6]=[CH:7][CH:8]=1.CS(O[CH2:15][CH2:16][N:17]=[N+:18]=[N-:19])(=O)=O.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[N:17]([CH2:16][CH2:15][N:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]1=[O:9])=[N+:18]=[N-:19]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 887313-Methoxy-2-pyridoneHCID 112751972-Azidoethyl methanesulfonate

생성물 1

HCID 866750871-(2-Azidoethyl)-3-methoxypyridine-2-one수율 55%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3-methoxypyridine-2-one (0.40 g, 3.20 mmol), 156a (0.79 g, 4.80 mmol), and K2CO3 (1.32 g, 9.60 mmol) stirred overnight in THF at reflux temperature. Reaction mixture was cooled down to room temperature. Reaction mixture was partitioned between CH2Cl2 (60 mL) and water (50 mL). Organic layer washed with water (2×35 mL), brine (1×30 mL). Organic layer dried on Na2SO4 and evaporated in vacuo. Crude product was purified by flash chromatography with stepwise gradient of CH2Cl2 and acetone (max 15%) to give 0.34 mg of 157a (55%) as colorless oil. 1H NMR (400 MHz, CDCl3) δ 6.77 (dd, J=6.9, 1.6 Hz, 1H), 6.48 (dd, J=7.5, 1.6 Hz, 1H), 5.96 (m, 1H), 3.91 (m, 2H), 3.62 (s, 3H), 3.52 (m, 2H). 13C NMR (100 MHz, CDCl3) δ 157.39, 149.41, 128.61, 112.16, 104.37, 55.36, 49.00, 48.91. HRMS (EI) calcd for C8H10N4O2 [M]+ 194.0804. found 194.0816.

후처리

  1. temperatureat reflux temperature
  2. customReaction mixture
  3. customReaction mixture
  4. customwas partitioned between CH2Cl2 (60 mL) and water (50 mL)
  5. washOrganic layer washed with water (2×35 mL), brine (1×30 mL)
  6. customOrganic layer dried on Na2SO4
  7. customevaporated in vacuo
  8. customCrude product was purified by flash chromatography with stepwise gradient of CH2Cl2 and acetone (max 15%)

출처 및 근거

ORD 기록
ord-2cdb65e1812e440cb74feba4164ae8ca
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871728B2

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