Potassium Phosphate, Tribasic → HCID 66913232, compound

HRID 2104484Notes

Reaction equation

HRID 2104484 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:8]2OS(C(F)(F)F)(=O)=O.[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>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.O1CCOCC1>[C:28]1([C:8]2[C:7]3[C:12](=[C:3]([C:2]([F:27])([F:26])[F:1])[CH:4]=[CH:5][CH:6]=3)[N:11]=[CH:10][C:9]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 66827Phenylboronic AcidHCID 86598744HCID 86598744, compound

Product 1

HCID 66913232HCID 66913232, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 8-(trifluoromethyl)-4-{[(trifluoromethyl)sulfonyl]oxy}quinoline-3-carboxylate (45.6 g, 109.3 mmol) was taken into dioxane (500 mL). Then phenylboronic acid (26.7 g, 218.6 mmol), K3PO4 (69.6 g, 327.9 mmol) and Pd(PPh3)4 (6.3 g, 5.5 mmol) was added and the reaction was brought to reflux for 1 hour. The reaction was filtered through Celite was still warm and concentrated. The resulting material was passed through a short silica gel plug and concentrated to yield the desired product as a brown viscous liquid (35.96 g). MS (ESI) m/z 346 ([M+H]+).

Workup

  1. temperatureto reflux for 1 hour
  2. filtrationThe reaction was filtered through Celite
  3. temperaturewas still warm
  4. concentrationconcentrated
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-48a90721103c473e8e1003d6fb815bbd
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

Loading…