Sodium Carbonate → HCID 66679841, compound

HRID 1842575Notes

Reaction equation

HRID 1842575 reaction equation
I[C:2]1[O:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([I:7])[N:6]=1.[CH3:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].C([O-])(O)=O.[Na+]>O1CCOCC1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[I:7][C:5]1[N:6]=[C:2]([C:17]2[CH:18]=[CH:19][C:14]([CH3:13])=[CH:15][CH:16]=2)[O:3][C:4]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 516892Sodium BicarbonateHCID 10596718HCID 10596718, compound

Product 1

HCID 66679841HCID 66679841, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of ethyl 2,4-diiodo-1,3-oxazole-5-carboxylate (0.13 g, 0.32 mmol), (4-methylphenyl)boronic acid (48.0 mg, 0.35 mmol) and sodium carbonate (2.0 M; 0.40 mL, 0.80 mmol) in dioxane (2 mL) was added dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (13.1 mg, 16.0 μmol). The mixture was stirred at ambient temperature. After 18 h, sat. NaHCO3 was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts was dried over MgSO4, filtered and concentrated. Purification by silica gel chromatography (100% hexanes 50% hexanes/ethyl acetate) gave the title compound (40 mg). MS 357.0 (M+1).

Workup

  1. extractionthe mixture was extracted with dichloromethane (3×)
  2. dry with materialThe combined organic extracts was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (100% hexanes 50% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-745a2d32721346c48b20fdda2e5f4d7f
Source dataset
uspto-grants-2015_02
Patent number
US08946231B2

Reaction notes

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