Ethanol → HCID 10474077, compound

HRID 902029Notes

Reaction equation

HRID 902029 reaction equation
[H-].[Na+].Cl[C:4]1[N:9]=[C:8]([C:10]2[C:18]([C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][N:12]3[N:11]=2)[CH:7]=[CH:6][CH:5]=1.[CH2:29]([OH:31])[CH3:30]>>[CH2:29]([O:31][C:4]1[N:9]=[C:8]([C:10]2[C:18]([C:19]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][N:12]3[N:11]=2)[CH:7]=[CH:6][CH:5]=1)[CH3:30]

Participants

4

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 59700605HCID 59700605, compound

Product 1

HCID 10474077HCID 10474077, compoundYield 94%

Conditions

Temperature
0 °C

Procedure

Add sodium hydride (25.5 mg, 0.64 mmol) to a solution of 4-[2-(6-chloro-pyridin-2-yl)-pyrazolo[1,5-a]pyridin-3-yl]-quinoline (50 mg, 0.14 mmol) in ethanol (2.5 mL) at 0° C. Stir the reaction mixture at 0° C. for 10 minutes, room temperature for 10 minutes more, and reflux overnight. Cool the reaction mixture to room temperature, quench with saturated aqueous ammonium chloride (3 mL). Add water (20 mL) and extract the aqueous solution with methylene chloride (3×20 mL). Dry the combined organic layers with sodium sulfate and purify by flash column chromatography (SiO2, 50% ethyl acetate/hexanes) to give the title compound 48 mg (94%) as an off-white solid.

Workup

  1. waitroom temperature for 10 minutes more
  2. temperaturereflux overnight
  3. temperatureCool the reaction mixture to room temperature
  4. customquench with saturated aqueous ammonium chloride (3 mL)
  5. extractionAdd water (20 mL) and extract the aqueous solution with methylene chloride (3×20 mL)
  6. dry with materialDry the combined organic layers with sodium sulfate
  7. custompurify by flash column chromatography (SiO2, 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f9ae9965496e4de29fa7f26c49e90d79
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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