Sodium hydride → HCID 86717603, compound

HRID 1616336Notes

Reaction equation

HRID 1616336 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[H-].[Na+].CS(O[CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)(=O)=O>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)[N:6]=[CH:5]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 126391895-Methyl-1H-indazole

Product 1

HCID 86717603HCID 86717603, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 5-methylindazole (901 mg) in DMF (10 mL) was added sodium hydride (327 mg) at 0° C., and the mixture was stirred with heating at 40° C. for 30 minutes. To the reaction solution was added tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (2.28 g), and the mixture was stirred with heating at 90° C. for 19 hours. Then, the mixture was partitioned between ethyl acetate and water, and the organic layer was washed with brine and dried over Na2SO4. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:5 as the eluting solvent) to give Compound Q1 (1.04 g).

Workup

  1. stirringthe mixture was stirred
  2. temperaturewith heating at 90° C. for 19 hours
  3. customThen, the mixture was partitioned between ethyl acetate and water
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate
  7. customhexane=2:5 as the eluting solvent) to give Compound Q1 (1.04 g)

Sources & evidence

ORD record
ord-96d3bd91be874713b3f5f9545dc0551d
Source dataset
uspto-grants-2014_07
Patent number
US08765786B2

Reaction notes

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