Potassium Phosphate, Tribasic → HCID 67398296, compound

HRID 714644Notes

Reaction equation

HRID 714644 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cl:12][C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1B(O)O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2N(C)C)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:12][C:13]1[C:18]([Cl:19])=[CH:17][CH:16]=[CH:15][C:14]=1[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

9

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 27346612,3-Dichlorobenzeneboronic acidHCID 38477682-Bromo-isonicotinic acid methyl ester

Product 1

HCID 67398296HCID 67398296, compound

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Under an atmosphere of argon, 250 mg (1.16 mmol) of methyl 2-bromoisonicotinate and 331 mg (1.74 mmol) of 2,3-dichlorophenylboronic acid were dissolved in 5 ml of toluene. 53 mg (0.06 mmol) of tris(dibenzylideneacetone)dipalladium, 46 mg (0.12 mmol) of 2-dicyclohexylphosphino-2′-(N,N-dimethylamino)biphenyl and 491 mg (2.31 mmol) of potassium phosphate were then added, and under argon the mixture was heated to 110° C. for 20 h. For work-up, the mixture was diluted at RT with 15 ml of ethyl acetate and 15 ml of water, the organic phase was separated off and the aqueous phase was extracted two more times with in each case 15 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was purified chromatographically [Method 19]. This gave 138 mg (42% of theory) of the target compound in a purity of 87%.

Workup

  1. customthe organic phase was separated off
  2. extractionthe aqueous phase was extracted two more times with in each case 15 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified chromatographically [Method 19]

Sources & evidence

ORD record
ord-21926ee3fad8455bac01a8b82f7d86c0
Source dataset
uspto-grants-2015_11
Patent number
US09187466B2

Reaction notes

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