Potassium Fluoride → HCID 67341853, compound

HRID 1669298Notes

Reaction equation

HRID 1669298 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH2:7][CH2:8][NH:9][C:10](=[O:33])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]([C:26]2[CH:27]=[N:28][C:29](Cl)=[CH:30][CH:31]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[F:35][C:36]([F:47])([F:46])[C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1.[F-].[K+]>C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:34])[CH2:7][CH2:8][NH:9][C:10](=[O:33])[C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]([C:26]2[CH:27]=[N:28][C:29]([C:40]3[CH:41]=[CH:42][C:37]([C:36]([F:47])([F:46])[F:35])=[CH:38][CH:39]=3)=[CH:30][CH:31]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 59729386HCID 59729386, compound

Product 1

HCID 67341853HCID 67341853, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-{4-[2-(6-Chloro-pyridin-3-yl)-octyloxy]-benzoylamino}-propionic acid tert-butyl ester (180 mg, 0.369 mmol) is dissolved in toluene (2.5 mL), followed by palladium tetrakis triphenylphosphine (23 mg, 0.0197 mmol), 4-trifluoromethyl-phenyl boronic acid (81 mg, 0.43 mmol), and potassium fluoride (46 mg, 0.75 mmol). The reaction is purged with nitrogen and heated to reflux, then the water (2.5 mL) is added. The reaction is monitored by HPLC, and upon completion, allowed to cool to room temperature. The reaction is diluted with EtOAc and then celite added, followed by water. This mixture is then filtered through a pad of celite. The solution is separated in a separatory funnel, then the organic layer is washed with 0.1N sodium hydroxide, water, and brine. The organic layer is dried over anhydrous sodium sulfate, then concentrated. The product is purified by flash column chromatography (110 mg).

Workup

  1. customThe reaction is purged with nitrogen
  2. temperatureheated
  3. temperatureto reflux
  4. additionthe water (2.5 mL) is added
  5. additionThe reaction is diluted with EtOAc
  6. additioncelite added
  7. filtrationThis mixture is then filtered through a pad of celite
  8. customThe solution is separated in a separatory funnel
  9. washthe organic layer is washed with 0.1N sodium hydroxide, water, and brine
  10. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  11. concentrationconcentrated
  12. customThe product is purified by flash column chromatography (110 mg)

Sources & evidence

ORD record
ord-d14def9185374801bf2d3fa9486e494d
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

Loading…