Potassium Carbonate → HCID 11608504, compound

HRID 1790121Notes

Reaction equation

HRID 1790121 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].C([O-])([O-])=O.[K+].[K+].Br[CH2:20][CH:21]([O:24][CH3:25])[O:22][CH3:23]>CN(C=O)C>[CH3:23][O:22][CH:21]([O:24][CH3:25])[CH2:20][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[CH:7]=[N:8]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 215015-NitroindazoleHCID 816722-Bromo-1,1-dimethoxyethane

Product 1

HCID 11608504HCID 11608504, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To a stirred mixture of 3.00 g (18.4 mmol) of 5-nitroindazole and 5.08 g (36.9 mmol) of K2CO3 in 61 mL of DMF was slowly added 3.42 g (20.2 mmol) of 2-bromo-1,1-dimethoxy-ethane and the mixture heated to 55° C. for 12 hours. The mixture was cooled to room temperature, filtered through a bed of celite. The filtrate was evaporated to dryness and the residue purified via column chromatography (30–80% ethyl acetate/hexanes) to provide 1.08 g of the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 3.25 (m, 6 H), 4.61 (d, J=5.43 Hz, 2 H), 4.78 (t, J=5.43 Hz, 1 H), 7.91 (m, 1 H), 8.23 (m, 1 H), 8.43 (s, 1 H), 8.82 (m, 1 H); MS (DCI/NH3) m/z 252 [M+H]+.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through a bed of celite
  3. customThe filtrate was evaporated to dryness
  4. customthe residue purified via column chromatography (30–80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-f46c721654e54331946496b18bc9053b
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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