Potassium Carbonate → HCID 57761071, compound

HRID 230936Notes

Reaction equation

HRID 230936 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][CH:18]=[CH:17][N:16]=3)[CH2:11][CH2:10]2)[N:5]=[C:4]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[N:3]=1.[Cl:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][C:37]=1[F:38].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.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>[Cl:31][C:32]1[CH:33]=[C:34]([C:2]2[C:7]([CH3:8])=[C:6]([N:9]3[CH2:14][CH2:13][N:12]([C:15]4[C:20]([C:21]([F:23])([F:22])[F:24])=[CH:19][CH:18]=[CH:17][N:16]=4)[CH2:11][CH2:10]3)[N:5]=[C:4]([N:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[N:3]=2)[CH:35]=[CH:36][C:37]=1[F:38]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 57761798HCID 57761798, compound

Product 1

HCID 57761071HCID 57761071, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-(4-chloro-5-methyl-6-{4-[3-(trifluoromethyl)(2-pyridyl)]piperazinyl}pyrimidin-2-yl)morpholine (66 mg, 0.15 mmol), 3-chloro-4-fluorophenylboronic acid (35 mg, 0.2 mmol), Pd(PPh3)4 (10 mg) and 2M potassium carbonate (0.2 mL) in toluene (3 mL) is heated, under a nitrogen atmosphere, at 80° C. for 4 hours. The reaction mixture is cooled and the layers separated. The aqueous layer is extracted with EtOAc (3×10 mL) and the combined organics washed with 4M NaOH (10 mL), water (10 mL), brine (10 mL), dried (MgSO4) and concentrated under reduced pressure. The residue is purified by flash chromatography on silica gel (70% hexane/30% ether) to give the title compound. MS 537 (M+1).

Workup

  1. temperatureThe reaction mixture is cooled
  2. customthe layers separated
  3. extractionThe aqueous layer is extracted with EtOAc (3×10 mL)
  4. washthe combined organics washed with 4M NaOH (10 mL), water (10 mL), brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe residue is purified by flash chromatography on silica gel (70% hexane/30% ether)

Sources & evidence

ORD record
ord-7f80605c1e7549eaa48d67495ca2057b
Source dataset
uspto-grants-2009_07
Patent number
US07566712B2

Reaction notes

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