Cesium carbonate → Tert-butyl 4-[(5-bromo-4-methyl-2H-indazol-2-yl)methyl]piperidin-1-carboxylate

HRID 2174923Notes

Reaction equation

HRID 2174923 reaction equation
[Br:1][C:2]1[C:3]([CH3:11])=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[C:18]([N:25]1[CH2:30][CH2:29][CH:28]([CH2:31]Br)[CH2:27][CH2:26]1)([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[CH:9][C:8]2[C:4](=[CH:5][N:6]([CH2:31][CH:28]3[CH2:29][CH2:30][N:25]([C:18]([O:20][C:21]([CH3:22])([CH3:24])[CH3:23])=[O:19])[CH2:26][CH2:27]3)[N:7]=2)[C:3]=1[CH3:11]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 441192325-Bromo-4-methyl-1H-indazole

Product 1

HCID 117690409Tert-butyl 4-[(5-bromo-4-methyl-2H-indazol-2-yl)methyl]piperidin-1-carboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

5 g of 5-bromo-4-methyl-1H-indazole was dissolved in 110 ml DMF and treated with 11.5 g of caesium carbonate and 7.9 g of N-Boc-4-(bromomethyl)piperidine. The mixture was stirred for 3 hrs at 60° C. and overnight at RT. The reaction mixture was next diluted with ethyl acetate, and the organic phase was washed twice with water, dried over sodium sulphate, filtered and concentrated. The residue was purified chromatographically on the Biotage SP4 via a 65i-Si column Gradient: hexane/ethyl acetate 0-100%. Yield: 3.53 g of the title compound.

Workup

  1. washthe organic phase was washed twice with water
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified chromatographically on the Biotage SP4 via a 65i-Si column Gradient

Sources & evidence

ORD record
ord-0bb6e0007afe46bb9a2880c4863d4095
Source dataset
uspto-grants-2015_06
Patent number
US09062041B2

Reaction notes

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