Potassium Carbonate → 6-Chloro-4-(4-chloro-phenyl)-3-(2,2,2-trifluoro-ethoxy)-pyridazine

HRID 1528352Notes

Reaction equation

HRID 1528352 reaction equation
Br[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[O:9][CH2:10][C:11]([F:14])([F:13])[F:12].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:8][C:6]1[N:5]=[N:4][C:3]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[C:2]([C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)[CH:7]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 866631334-Bromo-6-chloro-3-(2,2,2-trifluoro-ethoxy)-pyridazine

Product 1

HCID 866631356-Chloro-4-(4-chloro-phenyl)-3-(2,2,2-trifluoro-ethoxy)-pyridazineYield 65.8%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 0.676 g 4-bromo-6-chloro-3-(2,2,2-trifluoro-ethoxy)-pyridazine, 363 mg 4-chlorophenylboronic acid, 641 mg potassium carbonate and 134 mg tetrakis(triphenylphosphine) palladium in 15 mL tetrahydrofuran and 15 mL water was heated to reflux for 18 h. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel using a gradient of heptane: ethyl acetate of 95:5 to 50:50 to yield 0.493 g of the title compound as white solid, MS 323.1 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. customThe phases were separated
  5. customthe organic phase was purified by chromatography on silica gel using a gradient of heptane

Sources & evidence

ORD record
ord-29475ea1339b4a7e9ac742c617185f06
Source dataset
uspto-grants-2015_07
Patent number
US09090599B2

Reaction notes

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