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

HRID 626331Notes

Reaction equation

HRID 626331 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-d90edb642f0846c6902bc7b2b3df2b37
Source dataset
uspto-grants-2016_04
Patent number
US09309221B2

Reaction notes

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