Sulfuric Acid → HCID 178439450, compound

HRID 1924323Notes

Reaction equation

HRID 1924323 reaction equation
[Br:1][C:2]1[C:3]([CH2:20][N:21]2[CH2:25][CH:24]([CH2:26][CH2:27][CH3:28])[CH2:23][C:22]2=[O:29])=[C:4]2[N:10]=[CH:9][N:8](CC3C=CC(OC)=CC=3)[C:5]2=[N:6][CH:7]=1.C1(OC)C=CC=CC=1.OS(O)(=O)=O.C([O-])(O)=O.[Na+]>FC(F)(F)C(O)=O.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([CH2:20][N:21]2[CH2:25][CH:24]([CH2:26][CH2:27][CH3:28])[CH2:23][C:22]2=[O:29])=[C:4]2[N:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 7519AnisoleHCID 516892Sodium BicarbonateHCID 53629192HCID 53629192, compound

Product 1

HCID 178439450HCID 178439450, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A solution containing 1-{[6-bromo-3-(4-methoxybenzyl)-3H-imidazo[4,5-b]pyridin-7-yl]methyl}-4-propylpyrrolidin-2-one x213 (0.5 g, 0.1 mmol), anisole (0.4 ml) and concentrated H2SO4 (0.2 ml) in trifluoroacetic acid (4 ml) is stirred in a flow of argon at 20° C. for 2 h. The homogeneous reaction mixture is added dropwise at 0° C. to a mixture of a saturated aqueous solution of NaHCO3 (50 ml) and ethyl acetate (50 ml). The organic layer is separated. The aqueous one (pH ˜8) is subjected to additional extraction with chloroform containing 10% of tert-butanol. The combined organic layers are dried with anhydrous sodium sulfate and evaporated. The residue is purified by chromatography on silicagel (chloroform/methanol) to afford 0.31 g of 1-[(6-bromo-3H-imidazo[4,5-b]pyridin-7-yl)methyl]-4-propylpyrrolidin-2-one 99.

Workup

  1. customThe organic layer is separated
  2. extractionThe aqueous one (pH ˜8) is subjected to additional extraction with chloroform containing 10% of tert-butanol
  3. dry with materialThe combined organic layers are dried with anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue is purified by chromatography on silicagel (chloroform/methanol)

Sources & evidence

ORD record
ord-df2248f85a0047dca80f006e83a3edf5
Source dataset
uspto-grants-2012_05
Patent number
US08178533B2

Reaction notes

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