Ethanol → 2-(4-Bromo-2,3-difluoro-phenyl)-pyrimidine

HRID 1038118Notes

Reaction equation

HRID 1038118 reaction equation
Br[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[C:11]([F:18])[C:10]=1[F:19].C(=O)([O-])[O-].[K+].[K+].C(O)C>C1(C)C=CC=CC=1.O.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>[Br:8][C:9]1[CH:14]=[CH:13][C:12]([C:2]2[N:7]=[CH:6][CH:5]=[CH:4][N:3]=2)=[C:11]([F:18])[C:10]=1[F:19]

Participants

9

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 783452-BromopyrimidineHCID 27732924-Bromo-2,3-difluorobenzeneboronic acid

Product 1

HCID 576859312-(4-Bromo-2,3-difluoro-phenyl)-pyrimidine

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-bromopyrimidine (2.0 g, 12.7 mmol), 4-bromo-2,3-difluorobenzeneboronic acid (1.0 g, 4.22 mmol), potassium carbonate (2.93 g, 21.1 mmol) in a mixture of toluene (30 ml)/ethanol (30 ml)/water (15 ml) were purged with nitrogen for 15 min. Tetrakis(triphenylphosphine)palladium(0) (488 mg, 0.42 mmol) was added and the mixture was stirred at 90° C. in a sealed-tube for overnight. The mixture was cooled to r.t. and was diluted with water and ethyl acetate. Layers were separated. The separated organic layer was dried (MgSO4), filtered and solvents were removed in vacuum. Column purification [Hexanes-Ethyl acetate, 2:1 (v/v)] gave bromide 3AC (0.97 g, 85%) as white solid.

Workup

  1. customwere purged with nitrogen for 15 min
  2. temperatureThe mixture was cooled to r.t.
  3. customLayers were separated
  4. dry with materialThe separated organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customsolvents were removed in vacuum
  7. customColumn purification [Hexanes-Ethyl acetate, 2:1 (v/v)]

Sources & evidence

ORD record
ord-5414e2b09a2c40629eb0f0a956f0615b
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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