Dimethylformamide → HCID 59700617, compound

HRID 902030Notes

Reaction equation

HRID 902030 reaction equation
[H-].[Na+].Cl[C:4]1[N:9]=[C:8]([C:10]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[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.CN([CH:29]=[O:30])C>CO>[F:25][C:22]1[CH:23]=[CH:24][C:19]([C:18]2[C:10]([C:8]3[CH:7]=[CH:6][CH:5]=[C:4]([O:30][CH3:29])[N:9]=3)=[N:11][N:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=23)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 85957072HCID 85957072, compound

Product 1

HCID 59700617HCID 59700617, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium hydride (20.7 mg, 60% dispersion in mineral oil, 0.52 mmol) to a solution of 2-(6-chloro-pyridin-2-yl)-3-(4-fluoro-phenyl)-pyrazolo[1,5-a]pyridine (33.5 mg, 0.10 mmol) in DMF (2.5 mL) and methanol (2.5 mL) at room temperature. Stir the reaction mixture at room temperature for 4 hours and at 80° C. for 48 hours. Cool to room temperature and concentrate in vacuo. Add water (20 mL) and extract the aqueous solution with methylene chloride (3×20 mL). Dry the combined organic layers with sodium sulfate and concentrate. Purify by flash column chromatography (SiO2, 50% ethyl acetate/hexanes) to give the title compound 31 mg (97%) as an off-white solid.

Workup

  1. waitat 80° C. for 48 hours
  2. temperatureCool to room temperature
  3. concentrationconcentrate in vacuo
  4. extractionAdd water (20 mL) and extract the aqueous solution with methylene chloride (3×20 mL)
  5. dry with materialDry the combined organic layers with sodium sulfate
  6. concentrationconcentrate
  7. customPurify by flash column chromatography (SiO2, 50% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-395892b590474283b2bebd6db676bd86
Source dataset
uspto-grants-2008_04
Patent number
US07365066B2

Reaction notes

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