Potassium Carbonate → 8-(Acetoxymethyl)-3-phenylimidazo[1,2-a]pyridine

HRID 1789210노트

반응식

HRID 1789210 반응식
[C:1]([O:4][CH2:5][C:6]1[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=1)(=[O:3])[CH3:2].Br[CH:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH:15]=O.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([O:4][CH2:5][C:6]1[C:7]2[N:8]([C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:15][N:12]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 108889012-Bromo-2-phenylacetaldehydeHCID 201888553-(Acetoxymethyl)-2-pyridinamine

생성물 1

HCID 201888468-(Acetoxymethyl)-3-phenylimidazo[1,2-a]pyridine수율 59.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 4.4 g (26 mmole) of 3-(acetoxymethyl)-2-pyridinamine and 6.0 g (30 mmole) of 2-bromo-2-phenylacetaldehyde was heated at 65°. The mixture was dissolved in water, made basic with aqueous potassium carbonate, and extracted with dichloromethane. The organic layer was washed with water, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with diethyl ether to yield 4.1 g of 8-(acetoxymethyl)-3-phenylimidazo[1,2-a]pyridine as confirmed by the nmr and infrared spectra and by elemental analysis. [Calcd. for C16H14N2O2 : C, 72.17; H, 5.30; N, 10.52. Found: C, 71.90; H, 5.25; N, 10.43.] The title compound (1.5 g) was prepared by the method described in Example 26 using 1.3 g (5 mmole) of 8-(acetoxymethyl)-3-phenylimidazo[1,2-a]pyridine instead of 8-hydroxymethyl-2-phenylimidazo[1,2-a]pyridine. Structure assignment was supported by the nmr and infrared spectra and by elemental analysis.

후처리

  1. temperaturewas heated at 65°
  2. extractionextracted with dichloromethane
  3. washThe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated with diethyl ether

출처 및 근거

ORD 기록
ord-ec4b142bf5f74761be211a314d93711e
출처 데이터셋
uspto-grants-1987_08
특허 번호
US04687775

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