Cesium carbonate → HCID 86704206, compound

HRID 624000Notes

Reaction equation

HRID 624000 reaction equation
Cl[CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[CH3:13].[N+:14]([C:17]1[CH:18]=[N:19][NH:20][CH:21]=1)([O-:16])=[O:15].C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH3:13][C:5]1[N:4]([CH2:3][CH2:2][N:19]2[CH:18]=[C:17]([N+:14]([O-:16])=[O:15])[CH:21]=[N:20]2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 6423259HCID 6423259, compound

Product 1

HCID 86704206HCID 86704206, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To 1-(2-chloroethyl)-2-methyl-1H-benzoimidazole) (4.42 g, 22.71 mmol), in MeCN (50 mL), 4-nitro-1H-pyrazole (2.57 g, 22.71 mmol) and Cs2CO3 (8.14 g, 24.98 mmol) was added. After stirring at 80° C. for 18 h the reaction mixture was allowed to reach rt and filtered. The filter cake was washed with DCM and the filtrate was concentrated in vacuo, then the residue was dissolved in DCM and washed with H2O. The combined aq. layers were reextracted with DCM, the combined org. layers were dried (MgSO4), filtered and the solvent removed under reduced pressure to yield 2-methyl-1-(2-(4-nitro-1H-pyrazol-1-yl)-ethyl)-1H-benzoimidazole, which is used in the next step without further purification. LC-MS conditions B: tR=0.42 min, [M+H]+=272.07.

Workup

  1. customto reach rt
  2. filtrationfiltered
  3. washThe filter cake was washed with DCM
  4. concentrationthe filtrate was concentrated in vacuo
  5. dissolutionthe residue was dissolved in DCM
  6. washwashed with H2O
  7. dry with materiallayers were dried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-7c6f659e98694446ab4e59224cdf9062
Source dataset
uspto-grants-2016_04
Patent number
US09303023B2

Reaction notes

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