Methanol → HCID 10360657, compound

HRID 902028Notes

Reaction equation

HRID 902028 reaction equation
[CH3:1][OH:2].[H-].[Na+].Cl[C:6]1[N:11]=[C:10]([C:12]2[C:20]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=[CH:23][CH:22]=3)=[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][N:14]3[N:13]=2)[CH:9]=[CH:8][CH:7]=1>CN(C=O)C>[CH3:1][O:2][C:6]1[N:11]=[C:10]([C:12]2[C:20]([C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=[CH:23][CH:22]=3)=[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][N:14]3[N:13]=2)[CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 59700605HCID 59700605, compound

Product 1

HCID 10360657HCID 10360657, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

Add methanol (19 mg, 0.59 mmol) and sodium hydride (14 mg, 60% dispersion, 0.35 mmol) to a solution of 4-[2-(6-chloro-pyridin-2-yl)-pyrazolo[1,5-a]pyridin-3-yl]-quinoline (42 mg, 0.118 mmol) in DMF (0.6 mL) at room temperature. Heat to 110° C. for 3 hours, cool to room temperature, and quench with saturated aqueous ammonium chloride (0.5 mL). Concentrate in vacuo, filter, and purify by flash column chromatography (Silica Gel, 20-40% acetone/hexanes) to provide the title compound 30 mg (73%) as a white solid.

Workup

  1. temperaturecool to room temperature
  2. customquench with saturated aqueous ammonium chloride (0.5 mL)
  3. concentrationConcentrate in vacuo
  4. filtrationfilter
  5. custompurify by flash column chromatography (Silica Gel, 20-40% acetone/hexanes)

Sources & evidence

ORD record
ord-4be8636446884363b61e46ee11a45cfc
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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