Benzenesulfinic acid → HCID 66599996, compound

HRID 1621990Notes

Reaction equation

HRID 1621990 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.[C:9]1([S:15]([OH:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[Na].N1CCC[C@H]1C(O)=O.[OH-].[Na+]>CCOC(C)=O.[Cu]I.CS(C)=O>[C:9]1([S:15]([C:2]2[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=2)(=[O:17])=[O:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

9

Reactant 5

HCID 12057Benzenesulfinic acidHCID 14798Sodium HydroxideHCID 145742L-ProlineHCID 8176813-Amino-5-bromopyridineHCID 5360545Sodium

Product 1

HCID 66599996HCID 66599996, compoundYield 11%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To 5-bromopyridin-3-amine (1.59 g, 9.19 mmol) (Aldrich) was added benzenesulfinic acid, sodium salt (1.810 g, 11.03 mmol) (Sigma-Aldrich), copper(I) iodide (0.175 g, 0.919 mmol), (S)-pyrrolidine-2-carboxylic acid (0.212 g, 1.838 mmol), sodium hydroxide (0.074 g, 1.838 mmol), and DMSO (18 mL), and the resulting mixture was stirred at 100° C. for 3 days. The reaction mixture was then diluted with 200 mL of EtOAc, added to a separatory funnel, and partitioned with sodium bicarbonate (saturated, aqueous). The organic layer was separated, washed 4 times with 150 mL of sodium bicarbonate (saturated, aqueous), dried over sodium sulfate, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, 0% to 3% (2 M ammonia in MeOH)/DCM) furnished the title compound (11% yield). m/z (ESI, +ve ion) 235.3 (M+H)+.

Workup

  1. additionadded to a separatory funnel
  2. custompartitioned with sodium bicarbonate (saturated, aqueous)
  3. customThe organic layer was separated
  4. washwashed 4 times with 150 mL of sodium bicarbonate (saturated, aqueous)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customChromatographic purification of the residue (silica gel, 0% to 3% (2 M ammonia in MeOH)/DCM)

Sources & evidence

ORD record
ord-2cb1ab22f21e4ec1bf8070436d168be2
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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