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

HRID 1025948Notes

Reaction equation

HRID 1025948 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-23efa5f5304d4d71bba9dfcf8a7c9d6e
Source dataset
uspto-grants-2014_05
Patent number
US08729105B2

Reaction notes

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