Potassium Phosphate, Tribasic → HCID 86683044, compound

HRID 1497223Notes

Reaction equation

HRID 1497223 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]#[N:14])=[C:5]2OS(C(F)(F)F)(=O)=O.[CH:23]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)([CH3:25])[CH3:24].[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>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[C:6]([C:13]#[N:14])=[C:5]2[C:30]1[CH:29]=[CH:28][CH:27]=[C:26]([CH:23]([CH3:25])[CH3:24])[CH:31]=1

Participants

7

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27734783-Isopropylbenzeneboronic acidHCID 86683043HCID 86683043, compound

Product 1

HCID 86683044HCID 86683044, compound

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

A mixture of trifluoro-methanesulfonic acid 6-chloro-3-cyano-2-oxo-1,2-dihydro-quinolin-4-yl ester (400 mg, 1.13 mmol, Eq: 1.00), 3-isopropylphenylboronic acid (223 mg, 1.36 mmol, Eq: 1.2), potassium phosphate tribasic (361 mg, 1.7 mmol, Eq: 1.5) and tetrakis(triphenylphosphine)palladium (0) (65.5 mg, 56.7 μmol, Eq: 0.05) in dioxane (8.00 ml) was heated to 100° C. for 4 h. The reaction mixture was cooled to RT, diluted with sat. NH4Cl solution and extracted with ethyl acetate (2×). The combined extracts were washed with sat. NH4Cl solution and brine, dried with Na2SO4 and evaporated. Diethylether was added to the remaining red solid and the mixture was stirred for 2 h. Then the orange solid was filtered off (222 mg). MS (ESI): 323.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionextracted with ethyl acetate (2×)
  3. washThe combined extracts were washed with sat. NH4Cl solution and brine
  4. dry with materialdried with Na2SO4
  5. customevaporated
  6. additionDiethylether was added to the remaining red solid
  7. filtrationThen the orange solid was filtered off (222 mg)

Sources & evidence

ORD record
ord-0a098b883b144092975335d8a44c45df
Source dataset
uspto-grants-2015_12
Patent number
US09199938B2

Reaction notes

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