Potassium Carbonate → HCID 68610220, compound

HRID 515372Notes

Reaction equation

HRID 515372 reaction equation
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].[N+:25]([C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[NH:33][N:32]=[CH:31]2)([O-:27])=[O:26]>CN(C)C=O.C(OCC)(=O)C>[N+:25]([C:28]1[CH:29]=[C:30]2[C:34](=[CH:35][CH:36]=1)[N:33]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)[N:32]=[CH:31]2)([O-:27])=[O:26]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Product 1

HCID 68610220HCID 68610220, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (30.6 mmol, 8.56 g), potassium carbonate (61.3 mmol, 8.47 g) and 5-nitro-1H-indazole (30.6 mmol, 5 g) were combined and heated to 100° C. in N,N-dimethylformamide (30 mL) for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was dried over sodium sulfate and concentrated at reduced pressure. The resulting residue was purified by silica chromatography (eluting with a solvent gradient from dichloromethane to 30% ethyl acetate/heptane to 50% ethyl acetate/heptane) to afford the title compound (2.35 g). MS (ESI) m/z 291.0 [M+H]+

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated at reduced pressure
  4. customThe resulting residue was purified by silica chromatography (
  5. washeluting with a solvent gradient from dichloromethane to 30% ethyl acetate/heptane to 50% ethyl acetate/heptane)

Sources & evidence

ORD record
ord-74a3fe2e6e6d4626bd07c2ed20e37849
Source dataset
uspto-grants-2015_08
Patent number
US09108939B2

Reaction notes

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