Carbon Dioxide → HCID 178438000, compound

HRID 1880377Notes

Reaction equation

HRID 1880377 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[C:5]2[CH2:11][CH3:12].[Li]C(C)(C)C.[C:18](=[O:20])=[O:19]>C(OCC)C>[CH2:11]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:18]([OH:20])=[O:19])[CH:3]=2)[NH:7][N:6]=1)[CH3:12]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 178418306HCID 178418306, compoundHCID 178437989HCID 178437989, compound

Product 1

HCID 178438000HCID 178438000, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a −78° C. solution of 5-bromo-3-ethyl-1H-indazole (5 g, 22 mmol) in diethyl ether (150 mL) was added t-BuLi (4.84 g, 75.6 mmol). The mixture was stirred at −78° C. for 1 hour. Dry CO2 gas was passed through the reaction mixture at −78° C. for 1 hour and the temperature was slowly raised to room temperature for 2 hours. The reaction mixture was stirred at room temperature for 1 hour and quenched with saturated NH4Cl solution. The ether layer was separated and concentrated to recover unreacted starting material. The pH of the aqueous layer was made acidic with 2 N HCl, which was filtered to afford the title compound (2 g, 47%) as a pale brown solid. 1H NMR (DMSO-d6): δ12.6-13.0 (br, 2H), 8.4 (s, 1H), 7.9 (d, 1H), 7.5 (d, 1H), 3.0 (q, 2H), 1.4 (t, 3H).

Workup

  1. temperaturethe temperature was slowly raised to room temperature for 2 hours
  2. stirringThe reaction mixture was stirred at room temperature for 1 hour
  3. customquenched with saturated NH4Cl solution
  4. customThe ether layer was separated
  5. concentrationconcentrated
  6. customto recover unreacted
  7. filtrationwas filtered

Sources & evidence

ORD record
ord-36e799df610043258521840d2d6a6237
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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