Potassium Phosphate, Tribasic → HCID 86682997, compound

HRID 1497157Notes

Reaction equation

HRID 1497157 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH:25]([CH3:27])[CH3:26])=[N:7][C:8]2[C:13]([C:14]=1OS(C(F)(F)F)(=O)=O)=[CH:12][C:11]([Cl:23])=[CH:10][C:9]=2[Cl:24])=[O:4].[Cl:28][C:29]1[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][C:34]=1[F:35].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.[NH4+].[Cl-].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>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH:25]([CH3:26])[CH3:27])=[N:7][C:8]2[C:13]([C:14]=1[C:31]1[CH:32]=[CH:33][C:34]([F:35])=[C:29]([Cl:28])[CH:30]=1)=[CH:12][C:11]([Cl:23])=[CH:10][C:9]=2[Cl:24])=[O:4]

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27346603-Chloro-4-fluorophenylboronic Acid (contains varying amounts of Anhydride)HCID 86682995HCID 86682995, compound

Product 1

HCID 86682997HCID 86682997, compoundYield 59.6%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 25517Ammonium ChlorideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A suspension of 6,8-dichloro-2-isopropyl-4-trifluoromethanesulfonyloxy-quinoline-3-carboxylic acid methyl ester (85.0 mg, 0.181 mmol, Eq: 1.00), 3-chloro-4-fluorophenylboronic acid (34.7 mg, 0.199 mmol, Eq: 1.1), potassium phosphate tribasic (57.7 mg, 0.272 mmol, Eq: 1.5) and tetrakis(triphenylphosphine)palladium (0) (6.27 mg, 0.00543 mmol, Eq: 0.0300) in dioxane (2.5 ml) was heated to 100° C. for 4 h. The suspension was cooled to RT overnight, then diluted with sat. NH4Cl solution and extracted with ethyl acetate (3×). The combined organic layers were washed with sat. NH4Cl solution and brine, dried with Na2SO4 and evaporated. The remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 99:1) to afford the title compound as white solid (46 mg). MS (ESI): 426.0 (M+H)+.

Workup

  1. temperatureThe suspension was cooled to RT overnight
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined organic layers were washed with sat. NH4Cl solution and brine
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. customThe remaining residue was purified by column chromatography (silica gel, heptane/EtOAc 99:1)

Sources & evidence

ORD record
ord-a8352a54bb7d4ec8bfdfdc8ac49a7e20
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

Loading…