Cesium carbonate → HCID 66776329, compound

HRID 1644671Notes

Reaction equation

HRID 1644671 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-:3])=[O:2].Br[CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[N:8]=[CH:7]2)([O-:3])=[O:2].[N+:1]([C:4]1[CH:12]=[CH:11][C:10]2[C:6](=[CH:7][N:8]([CH2:14][CH2:15][CH2:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:9]=2)[CH:5]=1)([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 215015-NitroindazoleHCID 2596681-Bromo-4-phenylbutane

Product 2

HCID 66776329HCID 66776329, compoundHCID 66776382HCID 66776382, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 5-nitroindazole (1.098 g, 0.006731 mol), 1-bromo-4-phenylbutane (1.52 g, 0.00713 mol) and cesium carbonate (2.70 g, 0.00829 mol) in N,N-dimethylformamide (15 mL) was degassed with Ar for 10 min and then heated at 120° C. in a microwave for 50 min. The reaction was poured into water and extracted with methylene chloride (3×). The combined organics were washed with water and brine and then dried over MgSO4, filtered, and concentrated. The residue was purified by flash column chromatography to give the two regioisomers 5-nitro-1-(4-phenylbutyl)-1H-indazole and 5-nitro-2-(4-phenylbutyl)-2H-indazole as an inseparable mixture.

Workup

  1. customwas degassed with Ar for 10 min
  2. additionThe reaction was poured into water
  3. extractionextracted with methylene chloride (3×)
  4. washThe combined organics were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-c6054adc878449d9a9f6505470fa52ac
Source dataset
uspto-grants-2012_02
Patent number
US08124610B2

Reaction notes

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