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

HRID 539534ノート

反応式

HRID 539534 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 866750871-(2-Azidoethyl)-3-methoxypyridine-2-one収率 55%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-2cdb65e1812e440cb74feba4164ae8ca
出典データセット
uspto-grants-2014_10
特許番号
US08871728B2

反応ノート

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