Potassium Fluoride → HCID 67076810, compound

HRID 521498Notes

Reaction equation

HRID 521498 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8](Br)[C:7]([O:11][CH3:12])=[N:6][CH:5]=1.[CH:14]([C:17]1[CH:18]=[C:19](B(O)O)[CH:20]=[CH:21][CH:22]=1)([CH3:16])[CH3:15].F[B-](F)(F)F.C([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[F-].[K+]>O1CCOCC1.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]>[CH3:1][O:2][C:3](=[O:13])[C:4]1[CH:9]=[C:8]([C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([CH:14]([CH3:16])[CH3:15])[CH:22]=2)[C:7]([O:11][CH3:12])=[N:6][CH:5]=1

Participants

7

Reactant 4

HCID 522689Potassium FluorideHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 27734783-Isopropylbenzeneboronic acidHCID 46311221Methyl 5-bromo-6-methoxypyridine-3-carboxylate

Product 1

HCID 67076810HCID 67076810, compoundYield 54.4%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
45 °C

Procedure

Under an atmosphere of argon, a mixture of 5-bromo-6-methoxy-nicotinic acid methyl ester (W. J. Thompson and J. Gaudino, J. Org. Chem. 49 (1984), 5237-5243) (100 mg, 0.406 mmol), 3-isopropylphenylboronic acid (73 mg, 0.447 mmol), tri-(tert-butyl)phosphonium tetrafluoroborate (7 mg, 0.024 mmol), tris(dibenzylideneacetone)dipalladium(0) (11 mg, 0.012 mmol) and potassium fluoride (78 mg, 1.34 mmol) in a flask was suspended in dioxane (1.5 ml) and heated to 45° C. for 3 h. After cooling, it was filtered over a small plug of silica gel and evaporated to dryness. Purification of the residue by silica gel chromatography (HEP/EA gradient) and subsequent RP HPLC (water/ACN gradient) yielded 63 mg of the title compound.

Workup

  1. temperatureAfter cooling
  2. filtrationit was filtered over a small plug of silica gel
  3. customevaporated to dryness
  4. customPurification of the residue by silica gel chromatography (HEP/EA gradient) and subsequent RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-dc37b775a8cd4f02b1dc489223c88b87
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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