Potassium Carbonate → HCID 86760577, compound

HRID 1593489Notes

Reaction equation

HRID 1593489 reaction equation
[CH3:1][N:2]([CH:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]1)[C:3]([C:5]1[S:6][C:7]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[C:16](=[N:20][O:21][CH3:22])[CH2:15][CH2:14]3)=[C:8](Br)[CH:9]=1)=[O:4].[N:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>COCCOC.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][N:2]([CH:23]1[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]1)[C:3]([C:5]1[S:6][C:7]([C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[C:16](=[N:20][O:21][CH3:22])[CH2:15][CH2:14]3)=[C:8]([C:33]2[CH:34]=[CH:35][N:30]=[CH:31][CH:32]=2)[CH:9]=1)=[O:4]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 2734379(Pyridin-4-yl)boronic acidHCID 86760578HCID 86760578, compound

Product 1

HCID 86760577HCID 86760577, compoundYield 72%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

The product of Step 2 (670 mg, 1.4 mmol), 4-pyridyl boronic acid (M. Lamothe et al J. Med. Chem., 1997, 40, 3542) (189 mg, 1.5 mmol), potassium carbonate (1.17 g, 8.5 mmol), triphenylphosphine (37 mg, 0.14 mmol), and palladium acetate (16 mg, 0.07 mmol) were dissolved in ethylene glycol dimethyl ether (15 ml) and water (5 ml). The biphasic solution was heated at reflux for 16 hours, with vigorous stirring, cooled, then filtered through a pad of celite, which was thoroughly washed with ethyl acetate. The two phase filtrate was separated and the organic phase washed with saturated sodium bicarbonate solution, water (×3) and brine. The solution was dried over magnesium sulfate and evaporated in vacuo to a crude solid (691 mg), which was purified by silica gel chromatography (1:9:90 0.880 ammonia:ethanol:dichloromethane), to afford the title product, (476 mg, 72%); MS (AP+) m/e 475 [M+H]+

Workup

  1. temperatureThe biphasic solution was heated
  2. temperatureat reflux for 16 hours, with vigorous stirring
  3. temperaturecooled
  4. filtrationfiltered through a pad of celite, which
  5. washwas thoroughly washed with ethyl acetate
  6. customThe two phase filtrate was separated
  7. washthe organic phase washed with saturated sodium bicarbonate solution, water (×3) and brine
  8. dry with materialThe solution was dried over magnesium sulfate
  9. customevaporated in vacuo to a crude solid (691 mg), which
  10. customwas purified by silica gel chromatography (1:9:90 0.880 ammonia:ethanol:dichloromethane)

Sources & evidence

ORD record
ord-e03f154ce5d24a428cbc10982b88185f
Source dataset
uspto-grants-2007_11
Patent number
US07297693B2

Reaction notes

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