Cesium carbonate → HCID 86688442, compound

HRID 2359132Notes

Reaction equation

HRID 2359132 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[Cl:17][C:18]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=1[C@@H:25](Cl)[CH3:26]>CN1CCCC1=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[C@@H:25]([C:19]2[CH:20]=[CH:21][C:22]([Cl:24])=[CH:23][C:18]=2[Cl:17])[CH3:26])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 178424716-Bromo-1H-indazoleHCID 52420320HCID 52420320, compound

Product 1

HCID 86688442HCID 86688442, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 6-bromoindazole (3.4 g, 17.0 mmol) and Cs2CO3 (15.8 g, 48.5 mmol) in 1-methyl-2-pyrrolidinone (NMP, 11 mL) at 85° C. was added crude (S)-2,4-dichloro-1-(1-chloroethyl)benzene (3.2 g, 15.4 mmol) dropwise. The reaction mixture was heated for 10 min, and cooled to room temperature. The mixture was diluted with ethyl acetate (20 mL), washed with deionized water and brine, dried (Na2SO4), and concentrated in vacuo. The resulting crude material was purified by flash chromatography (SiO2, 5% ethyl acetate in hexanes) to afford (R)-6-bromo-1-(1-(2,4-dichlorophenyl)ethyl)-1H-indazole (2.2 g, 6.0 mmol, 39%).

Workup

  1. temperatureThe reaction mixture was heated for 10 min
  2. washwashed with deionized water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting crude material was purified by flash chromatography (SiO2, 5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6c3a31f9e3044243964402067a973d1c
Source dataset
uspto-grants-2014_04
Patent number
US08685959B2

Reaction notes

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