Methanesulfonic Acid → HCID 86647656, compound

HRID 1798693Notes

Reaction equation

HRID 1798693 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[N:6]1[C:7]([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[C:24](=[O:38])[C:25]([CH3:37])([CH3:36])[O:26][C:27]=3[C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)=[CH:19][CH:18]=2)=[CH:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12>C(Cl)Cl.C(OCC)C>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[N:6]1[C:7]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]3[C:24](=[O:38])[C:25]([CH3:36])([CH3:37])[O:26][C:27]=3[C:28]3[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=3)=[CH:21][CH:22]=2)=[CH:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=12

Participants

5

Reactant 2

HCID 6395Methanesulfonic AcidHCID 49778977HCID 49778977, compound

Product 1

HCID 86647656HCID 86647656, compoundYield 82.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Methanesulfonic acid (531 mg, 5.5 mmol) was added to a solution of 4-(4-(imidazo[1,2-a]pyridin-2-ylmethoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one (2.5 g, 5.5 mmol) in DCM (5 ml) and diethyl ether (150 mL) at RT under an atmosphere of nitrogen. The reaction mixture was stirred for a further 4 h at RT. The solids were collected by filtration, washed with 20% DCM in diethyl ether and dried in vacuo to afford 4-(4-(imidazo[1,2-a]pyridin-2-ylmethoxy)phenyl)-5-(4-methoxyphenyl)-2,2-dimethylfuran-3(2H)-one methanesulfonate (2.4 g, 82.7%) as white solid. 1H NMR: 500 MHz, DMSO-d6: δ 8.75 (d, 1H), 8.1 (s, 1H), 7.65 (Ar, 3H), 7.3-6.85 (Ar, 8H), 5.2 (s, 2H), 3.85 (s, 3H), 1.25 (s, 6H), HPLC: (98.8%, Condition-A).

Workup

  1. filtrationThe solids were collected by filtration
  2. washwashed with 20% DCM in diethyl ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-f2a215f81f1a4298b902570446f18535
Source dataset
uspto-grants-2013_01
Patent number
US08343973B2

Reaction notes

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