Potassium Carbonate → HCID 11622952, compound

HRID 1825831Notes

Reaction equation

HRID 1825831 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)C=O>[CH3:23][O:22][CH:21]([O:24][CH3:25])[CH2:20][N:8]1[CH:7]=[C:6]2[C:10]([CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5]2)=[N:9]1

Participants

5

Reactant 3

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

Product 1

HCID 11622952HCID 11622952, compoundYield 23.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

To mixture of 3.00 g (18.4 mmol) of 5-nitroindazole and 5.08 g (36.9 mmol) of K2CO3 in 61 mL of N,N-dimethylformamide and was added 3.42 g (20.2 mmol) of 2-bromo-1,1-dimethoxy-ethane. The mixture was heated to 55° C. and allowed to stir for 12 hours. The reaction mixture was cooled to room temperature and the contents filtered through a bed of celite. The filtrate was then concentrated under reduced pressure and the residue purified via column chromatography (30–80% ethyl acetate/hexanes) to provide 1.08 g of the title product. 1H NMR (400 MHz, DMSO-D6) δ ppm 3.31 (s, 6 H), 4.67 (d, J=5.49 Hz, 2 H), 4.91 (t, J=5.42 Hz, 1 H), 7.81 (m, 1.92 Hz, 1 H), 7.98 (m, 1 H), 8.62 (m, 2 H); MS (DCI/NH3) m/z 252 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. filtrationthe contents filtered through a bed of celite
  3. concentrationThe filtrate was then concentrated under reduced pressure
  4. customthe residue purified via column chromatography (30–80% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0910c0f42915481193ce92ddc03ce80c
Source dataset
uspto-grants-2006_05
Patent number
US07049307B2

Reaction notes

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