HCID 58515992, compound → HCID 58516000, compound

HRID 717857Notes

Reaction equation

HRID 717857 reaction equation
[CH3:1][Mg]Br.[Cl:4][C:5]1[C:6]2[N:7]([N:24]=[CH:25][CH:26]=2)[C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)=[C:9]([C:11](N(OC)C)=[O:12])[CH:10]=1>O1CCCC1>[Cl:4][C:5]1[C:6]2[N:7]([N:24]=[CH:25][CH:26]=2)[C:8]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)=[C:9]([C:11](=[O:12])[CH3:1])[CH:10]=1

Participants

4

Reactant 2

HCID 58515992HCID 58515992, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 58516000HCID 58516000, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

3.0 M Methylmagnesium bromide in tetrahydrofuran (0.87 mL) was added dropwise to a solution of 4-chloro-7-(3-fluorophenyl)-N-methoxy-N-methylpyrazolo[1,5-a]pyridine-6-carboxamide (0.25 g, 0.75 mmol) in tetrahydrofuran (3.038 mL) under N2 cooled to 0° C. The solution was stirred at 0° C. for 30 minutes. The reaction solution was quenched at 0° C. with 1.0 M hydrogen chloride in water (2.996 mL), poured into 25 mL of water saturated sodium bicarbonate solution and was extracted into ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo to give 1-[4-chloro-7-(3-fluorophenyl)pyrazolo[1,5-a]pyridin-6-yl]ethanone (0.15 g, 68%) as an oil. LCMS calculated for C15H11ClFN2O (M+H)+: m/z=289.1. found: 288.9.

Workup

  1. customThe reaction solution was quenched at 0° C. with 1.0 M hydrogen chloride in water (2.996 mL)
  2. additionpoured into 25 mL of water saturated sodium bicarbonate solution
  3. extractionwas extracted into ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ca5e350ebe7a41a8a3e9a7cb3c309010
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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