Ammonia → HCID 59803855, compound

HRID 253471Notes

Reaction equation

HRID 253471 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[N:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[CH3:11][S:12]([O-:14])=[O:13].[Na+].N1CCC[C@H]1C(O)=O.[OH-].[Na+].N>CS(C)=O.[Cu]I>[CH3:11][S:12]([C:2]1[CH:3]=[C:4]2[CH:5]=[CH:6][NH:7][C:8]2=[N:9][CH:10]=1)(=[O:14])=[O:13]

Participants

8

Reactant 5

HCID 222AmmoniaHCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 2733271Sodium methanesulfinateHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 59803855HCID 59803855, compoundYield 50.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To 5-bromo-7-azaindole (1, 1.00 g, 5.08 mmol) in dimethyl sulfoxide (15.0 mL) were added sodium methanesulfinate (0.622 g, 6.09 mmol), L-proline (0.117 g, 1.02 mmol), copper(I) iodide (0.200 g, 1.05 mmol), and sodium hydroxide (0.0406 g, 1.02 mmol). The reaction was stirred at 120° C. overnight. The reaction was poured into aqueous ammonia, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give the desired compound as a white solid (207, 0.50 g, 50.2%). MS (ESI) [M−H+]−=195.1.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. custompurified by silica gel column chromatography
  6. washeluting with 20% to 100% ethyl acetate in hexane

Sources & evidence

ORD record
ord-8a6fd31ff3404a07895b02af98a53221
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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