Methanesulfonic Acid → 5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one methanesulfonate

HRID 1798708Notes

Reaction equation

HRID 1798708 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].ClC1N2C=CC=CC2=NC=1COC1C=CC([C:24]2[C:25](=[O:39])[C:26]([CH3:38])([CH3:37])[O:27][C:28]=2[C:29]2[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=2)=CC=1>C(Cl)Cl.C(OCC)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[CH3:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([C:28]2[O:27][C:26]([CH3:37])([CH3:38])[C:25](=[O:39])[CH:24]=2)=[CH:34][CH:33]=1

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 497791154-(4-((3-chloroimidazo[1,2-a]pyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one

Product 1

HCID 866476605-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one methanesulfonateYield 159.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic acid (50.5 mg, 0.52 mmol) was added to a solution of 4-(4-((3-chloroimidazo[1,2-a]pyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (250 mg, 0.52 mmol) in DCM (2.5 ml) and diethyl ether (25 mL) at RT under an atmosphere of nitrogen. The reaction mixture was stirred at RT for 4 h upon which the compound was filtered, washed with 20% DCM in diethyl ether and dried in vacuo to afford 4-(4-(3-chloroimidazo[1,2-a]pyridin-2-yl)methoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one methanesulfonate (260 mg, 86%) as white solid. 1H NMR: 500 MHz, DMSO-d6: δ 8.55 (d, 1H), 8.0 (s, 1H), 7.65 (Ar, 3H), 7.3-6.85 (Ar, 7H), 5.2 (s, 2H), 3.85 (s, 3H), 2.15 (s, 3H) 1.25 (s, 6H), HPLC: (98.8%, Condition-A).

Workup

  1. filtrationwas filtered
  2. washwashed with 20% DCM in diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-4a63dc6502a94fa1ad28c532dc4f7352
Source dataset
uspto-grants-2013_01
Patent number
US08343973B2

Reaction notes

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