Sodium Methoxide → HCID 178495614, compound

HRID 1888223Notes

Reaction equation

HRID 1888223 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH2:24][CH2:25]Cl)(=[O:22])=[O:21])[CH2:16][CH2:15]1.[CH3:27][O-:28].[Na+]>CO.[I-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([C:11]([NH2:13])=[O:12])[CH:10]=1)[NH:7][N:6]=[C:5]2[CH:14]1[CH2:19][CH2:18][N:17]([S:20]([CH2:23][CH2:24][CH2:25][O:28][CH3:27])(=[O:22])=[O:21])[CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 178513508HCID 178513508, compound2×

Product 1

HCID 178495614HCID 178495614, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 5238Sodium IodideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5-bromo-3-{1-[(3-chloropropyl)sulfonyl]-4-piperidinyl}-1H-indazole-7-carboxamide (Intermediate 7) in MeOH (1.5 mL) were added 3.8 M sodium methoxide in MeOH (1 mL) and sodium iodide (5.0 mg). The reaction mixture was stirred at 80° C. overnight and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (15 mL) and washed with water (5 mL). The organic phase was collected, dried over MgSO4, filtered and concentrated to give the crude title compound (30 mg), which was used in the next step without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate (15 mL)
  3. washwashed with water (5 mL)
  4. customThe organic phase was collected
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-56974490a6904ac398485c722732c2e2
Source dataset
uspto-grants-2013_08
Patent number
US08501780B2

Reaction notes

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