Sodium hydride → HCID 67373425, compound

HRID 1253547Notes

Reaction equation

HRID 1253547 reaction equation
Br[C:2]1[CH:3]=[C:4]([OH:11])[C:5]2[N:6]([N:8]=[CH:9][CH:10]=2)[CH:7]=1.Br.Br[CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.[H-].[Na+]>CN(C=O)C>[CH3:7][N:6]1[CH:5]=[C:10]([C:2]2[CH:3]=[C:4]([O:11][CH2:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[C:5]3[N:6]([N:8]=[CH:9][CH:10]=3)[CH:7]=2)[CH:9]=[N:8]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 127070373-(Bromomethyl)pyridine hydrobromideHCID 67207447HCID 67207447, compound

Product 1

HCID 67373425HCID 67373425, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-bromopyrazolo[1,5-a]pyridin-4-ol (10.0 mg, 0.047 mmol), 3-(bromomethyl)pyridine hydrobromide (14.2 mg, 0.056 mmol), and NaH (6.7 mg, 0.168 mmol, 60 wt %) were suspended in DMF (1 ml) and stirred for 1 h. The reaction mixture was quenched by the addition of saturated aqueous ammonium chloride. The reaction mixture was diluted in ethyl acetate, then washed with water (5 mL) and brine (5 mL). The combined aqueous layers were extracted with ethyl acetate (2×10 mL), and the combined organic layers were dried over magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient) to afford 6-(1-methyl-1H-pyrazol-4-yl)-4-(pyridin-3-ylmethoxy)pyrazolo[1,5-a]pyridine.

Workup

  1. customThe reaction mixture was quenched by the addition of saturated aqueous ammonium chloride
  2. additionThe reaction mixture was diluted in ethyl acetate
  3. washwashed with water (5 mL) and brine (5 mL)
  4. extractionThe combined aqueous layers were extracted with ethyl acetate (2×10 mL)
  5. dry with materialthe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography on silica gel (methanol/ethyl acetate gradient)

Sources & evidence

ORD record
ord-469fb0c300ca4229bfbb91ab7061dc82
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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