5-bromo-1H-indazole → HCID 57095854, compound

HRID 1616341Notes

Reaction equation

HRID 1616341 reaction equation
CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[NH:13][N:12]=[CH:11]2.CS(O[CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1)(=O)=O>O1CCCC1>[Br:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1)[N:12]=[CH:11]2

Participants

5

Reactant 3

HCID 7619295-bromo-1H-indazoleHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 57095854HCID 57095854, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of potassium tert-butoxide (37.25 g) in tetrahydrofuran (1000 mL) was added 5-bromoindazole (54.52 g), and the mixture was stirred at room temperature for 15 minutes. To the reaction solution was added tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (98.74 g), and the reaction solution was heated at reflux for 1 day. 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=1:3 as the eluting solvent) to give Compound Q17 (45.68 g).

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureat reflux for 1 day
  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=1:3 as the eluting solvent) to give Compound Q17 (45.68 g)

Sources & evidence

ORD record
ord-e8e62c5fc5874e1f8a8ba2417737547a
Source dataset
uspto-grants-2014_07
Patent number
US08765786B2

Reaction notes

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