Toluene → HCID 67237867, compound

HRID 2363158Notes

Reaction equation

HRID 2363158 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[N:20]=[C:21](Cl)[O:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10].[CH2:25]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1B(O)O)[CH2:26][CH2:27][CH3:28].C([O-])([O-])=O.[Na+].[Na+].C1(C)C=CC=CC=1>CCOC(C)=O.O.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.C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:14]([NH:16][C:17]([C:19]2[N:20]=[C:21]([C:35]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:29][CH2:25][CH2:26][CH2:27][CH3:28])[O:22][CH:23]=2)=[O:18])[CH3:15])[CH:5]=[C:6]([F:13])[C:7]=1[NH:8][S:9]([CH3:12])(=[O:11])=[O:10]

Participants

9

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 50841002-Butoxyphenylboronic acidHCID 671108872-Chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide

Product 1

HCID 67237867HCID 67237867, compoundYield 39%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

In a glass tube were placed 2-chloro-oxazole-4-carboxylic acid [1-(3,5-difluoro-4-methanesulfonylamino-phenyl)-ethyl]-amide (100 mg, 0.26 mmol), 2-butoxy phenyl boronic acid (61 mg, 0.32 mmol), 2N—Na2CO3 (0.5 mL), Pd(PPh3)4 (4.6 mg, 0.004 mmol), toluene (1.0 mL), ethanol (0.5 mL), and a magnetic stir bar. The mixture was stirred overnight at 110° C. and was diluted with EtOAc and water. The organic layer was washed with saturated ammonium chloride, water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane) to give title compound (50 mg, 39%).

Workup

  1. customIn a glass tube were placed
  2. washThe organic layer was washed with saturated ammonium chloride, water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by column chromatography (gradient 12% to 100% EtOAc in n-hexane)

Sources & evidence

ORD record
ord-ba29fa53eacd4603bb8b37d0f92579a6
Source dataset
uspto-grants-2014_04
Patent number
US08691855B2

Reaction notes

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