Potassium Phosphate, Tribasic → HCID 86718102, compound

HRID 2205100Notes

Reaction equation

HRID 2205100 reaction equation
Cl[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([N:11]=1)=[CH:9][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=2.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.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>[C:16]1([C:3]2[C:2]([C:27]3[CH:28]=[CH:29][C:24]([C:23]([F:34])([F:33])[F:22])=[CH:25][CH:26]=3)=[N:11][C:10]3[C:5](=[CH:6][CH:7]=[C:8]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=3)[N:4]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 77231183Methyl 3-chloro-2-phenylquinoxaline-6-carboxylate

Product 1

HCID 86718102HCID 86718102, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

A suspension of methyl 3-chloro-2-phenylquinoxaline-6-carboxylate (100 mg, 0.33 mmol, 1.00 equiv), 4-(trifluoromethyl)phenylboronic acid (69.9 mg, 0.37 mmol, 1.10 equiv), K3PO4 (142 mg, 0.67 mmol, 2.00 equiv), Pd(PPh3)4 (11 mg, 0.01 mmol, 0.03 equiv) in toluene (1 mL) was placed in a 10-mL sealed tube under an inert atmosphere allowed to react, with stifling, overnight at 100° C. in an oil bath. The reaction was quenched by the addition of 20 mL of water, and the solids were collected by filtration, resulting in 80 mg (59%) of methyl 2-phenyl-3-(4-(trifluoromethyl)phenyl)quinoxaline-6-carboxylate as a yellow solid.

Workup

  1. customsealed tube under an inert atmosphere
  2. customto react
  3. customovernight
  4. customat 100° C.
  5. customThe reaction was quenched by the addition of 20 mL of water
  6. filtrationthe solids were collected by filtration
  7. customresulting in 80 mg (59%) of methyl 2-phenyl-3-(4-(trifluoromethyl)phenyl)quinoxaline-6-carboxylate as a yellow solid

Sources & evidence

ORD record
ord-1e8ee15e0c1e4b2c9afc4b08731cc8ca
Source dataset
uspto-grants-2016_06
Patent number
US09370522B2

Reaction notes

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