Potassium Carbonate → 7-(2,2-Dimethyl-propionyloxy)-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester

HRID 2388144Notes

Reaction equation

HRID 2388144 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9](Br)[C:8]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:14][C:7]=2[C:6]=1[O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[O:4].[CH3:28][O:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]([C:34]2[CH:33]=[CH:32][CH:31]=[C:30]([O:29][CH3:28])[CH:35]=2)[C:8]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:14][C:7]=2[C:6]=1[O:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[O:4].[CH3:1][O:2][C:3]([C:5]1[N:10]=[C:9]([C:34]2[CH:33]=[CH:32][CH:31]=[C:30]([O:29][CH3:28])[CH:35]=2)[C:8]2[N:12]=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[O:14][C:7]=2[C:6]=1[OH:21])=[O:4]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 2734370(3-Methoxyphenyl)boronic acidHCID 866481124-Bromo-7-(2,2-dimethyl-propionyloxy)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester

Product 2

HCID 675295117-(2,2-Dimethyl-propionyloxy)-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl esterHCID 675305517-Hydroxy-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Under a nitrogen atmosphere 4-bromo-7-(2,2-dimethyl-propionyloxy)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester (51 mg, 0.12 mmol), 3-methoxyphenylboronic acid (21.5 mg, 0.14 mmol), potassium carbonate (58.7 mg, 0.43 mmol), and tetrakis(triphenylphosphine)palladium(0) (20.4 mg, 0.018 mmol) were suspended in 3 mL of anhydrous 1,4-dioxane. The reaction mixture was heated at 100° C. for 16 hours, then cooled to room temperature, and diluted with ethyl acetate. The mixture was successively washed with water, saturated sodium bicarbonate, and brine solutions. The organic fraction was dried over anhydrous sodium sulfate and concentrated. The residue was purified by flash chromatography eluting from silica gel with a gradient of 0-50% ethyl acetate in hexanes to give 7.5 mg of 7-(2,2-Dimethyl-propionyloxy)-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester and 24.7 mg of 7-hydroxy-4-(3-methoxy-phenyl)-2-phenyl-oxazolo[4,5-c]pyridine-6-carboxylic acid methyl ester.

Workup

  1. temperaturecooled to room temperature
  2. washThe mixture was successively washed with water, saturated sodium bicarbonate, and brine solutions
  3. dry with materialThe organic fraction was dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting from silica gel with a gradient of 0-50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-adb1fb5ff8b44d0dbc54177f64566cb5
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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