Carbon Dioxide → HCID 178440407, compound

HRID 1880373Notes

Reaction equation

HRID 1880373 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][CH2:12][CH3:13].[Li]C(C)(C)C.[C:19](=[O:21])=[O:20]>C(OCC)C.CCCCC>[CH2:11]([C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:19]([OH:21])=[O:20])[CH:3]=2)[NH:7][N:6]=1)[CH2:12][CH3:13]

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 178418306HCID 178418306, compoundHCID 178440402HCID 178440402, compound

Product 1

HCID 178440407HCID 178440407, compoundYield 40.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Procedure

To 5-bromo-3-propyl-1H-indazole (1.00 g, 4.18 mmol) in diethyl ether (60 mL), 1.3 M t-BuLi (10.9 mL, 14.2 mmol) in pentane was added slowly at −78° C. under N2 atm. After 1 hour, CO2 gas was passed through the reaction mixture at −78° C. for 1 hour and allowed to slowly warm to room temperature. The reaction mixture was quenched with saturated NH4Cl solution and the ether layer was separated. The aqueous layer was acidified with 2 N HCl and extracted with ethyl acetate to afford the title compound (350 mg, 40.8%) as an off white solid. 1H NMR (DMSO-d6): δ 11.8-13.0 (br, 1H), 8.4 (s, 1H), 7.9 (d, 1H), 7.5 (d, 1H), 3.0 (q, 2H), 1.8 (q, 2H), 0.9 (t, 3H). mp: 296-299° C.

Workup

  1. customThe reaction mixture was quenched with saturated NH4Cl solution
  2. customthe ether layer was separated
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-a31c641937564ba1a491ede7635dfbb7
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

Loading…