Dimethylformamide → HCID 66689480, compound

HRID 592312Notes

Reaction equation

HRID 592312 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([C:11]([CH3:14])([CH3:13])[CH3:12])=[N:7][C:6]=2[CH:5]=[C:4]([C:15]([O:17][CH3:18])=[O:16])[CH:3]=1.[F:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1.C(NC(C)C)(C)C.CN(C)C=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Na+].[Na+].[Na+].P(C1C=C(S([O-])(=O)=O)C=CC=1)(C1C=C(S([O-])(=O)=O)C=CC=1)C1C=C(S([O-])(=O)=O)C=CC=1.C(OCC)(=O)C.O>[C:11]([C:8]1[O:9][C:10]2[C:2]([C:23]3[CH:24]=[CH:25][C:20]([F:19])=[CH:21][CH:22]=3)=[CH:3][C:4]([C:15]([O:17][CH3:18])=[O:16])=[CH:5][C:6]=2[N:7]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 7912DiisopropylamineHCID 2856454-Fluorophenylboronic acidHCID 66690849HCID 66690849, compound

Product 1

HCID 66689480HCID 66689480, compoundYield 91.5%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 6099338Trisodium 3,3',3''-phosphinetriyltris(benzene-1-sulphonate)CatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of methyl 7-bromo-2-tert-butyl-1,3-benzoxazole-5-carboxylate (218 mg, 0.698 mmol), (4-fluorophenyl)-boronic acid (0.147 g, 1.048 mmol), 3,3′,3″-phosphinidynetris (benzensulfonic acid) trisodium salt (34 mg, 0.052 mmol), palladium(II) acetate (3.92 mg, 0.017 mmol) and diisopropylamine (0.100 mL, 0.698 mmol) were added N,N-dimethylformamide (2.62 mL) and water (0.87 mL). The mixture was heated to 80° C. After 30 min, the mixture was cooled to ambient temperature and ethyl acetate was added. The organic layer was washed with water (3×), brine, dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→70% hexanes/ethyl acetate) gave the title compound (0.209 g). LC-MS [M+1]=328.3.

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. washThe organic layer was washed with water (3×), brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (100% hexanes→70% hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-f3ba7f13b6bf4310a911180551608931
Source dataset
uspto-grants-2016_01
Patent number
US09238647B2

Reaction notes

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