Potassium Carbonate → methyl 4'-methoxy-2-methyl-2''-[(4R,5R)-4-methyl-2-oxo-1,3-oxazolidin-5-yl]-4''-(trifluoromethyl)-1,1':3',1''-terphenyl-4-carboxylate

HRID 2093188Notes

Reaction equation

HRID 2093188 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C@H:12]1[O:16][C:15](=[O:17])[NH:14][C@@H:13]1[CH3:18].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([O:35][CH3:36])=[O:34])=[CH:29][C:28]=2[CH3:37])=[CH:23][C:22]=1B1OC(C)(C)C(C)(C)O1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O1CCOCC1>[CH3:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([O:35][CH3:36])=[O:34])=[CH:29][C:28]=2[CH3:37])=[CH:25][C:26]=1[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C@H:12]1[O:16][C:15](=[O:17])[NH:14][C@@H:13]1[CH3:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 57692976HCID 57692976, compound2×HCID 59726151(4R,5R)-5-[2-iodo-5-(trifluoromethyl)phenyl]4-methyl-1,3-oxazolidin-2-one2×

Product 1

HCID 67065997methyl 4'-methoxy-2-methyl-2''-[(4R,5R)-4-methyl-2-oxo-1,3-oxazolidin-5-yl]-4''-(trifluoromethyl)-1,1':3',1''-terphenyl-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

(4R,5R)-5-[2-iodo-5-(trifluoromethyl)phenyl]-4-methyl-1,3-oxazolidin-2-one (INTERMEDIATE 12, 100 mg, 0.269 mmol), methyl 4′-methoxy-2-methyl-3′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)biphenyl-4-carboxylate (INTERMEDIATE 11, 124 mg, 0.323 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium dichloride dichloromethane adduct (44 mg, 0.054 mmol), aqueous potassium carbonate (270 μL, 2M, 0.538 mmol) and 1,4-dioxane (2 mL) were sealed in a microwave vessel. The vessel was irradiated by microwave at 140° C. for 30 minutes. LCMS of the aliquot indicated complete consumption of starting iodide. The crude mixture was purified by SiO2 (preparative TLC plates, 50% ethyl acetate in hexanes) to give a glassy residue. The residue was further purified by SiO2 (preparative TLC plates, 10% ethyl acetate in dichloromethane) to afford methyl 4′-methoxy-2-methyl-2″-[(4R,5R)-4-methyl-2-oxo-1,3-oxazolidin-5-yl]-4″-(trifluoromethyl)-1,1′:3′,1″-terphenyl-4-carboxylate. LCMS calc.=499.16; found=500.08 (M+1).

Workup

  1. customThe vessel was irradiated by microwave at 140° C. for 30 minutes
  2. customconsumption of starting iodide
  3. customThe crude mixture was purified by SiO2 (preparative TLC plates, 50% ethyl acetate in hexanes)
  4. customto give a glassy residue
  5. customThe residue was further purified by SiO2 (preparative TLC plates, 10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-6543929599bd44089bab606ca520c74e
Source dataset
uspto-grants-2013_05
Patent number
US08440702B2

Reaction notes

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