Potassium Fluoride → HCID 67153562, compound

HRID 1914300Notes

Reaction equation

HRID 1914300 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][NH:6][C:7](=[O:29])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:21][C:22]2[CH:23]=[N:24][C:25](Cl)=[CH:26][CH:27]=2)[CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:10][CH:9]=1.[C:31]([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)([CH3:34])([CH3:33])[CH3:32].[F-].[K+].COC(=O)CCCC(C1C=CC(C(OC2C=NC(C3C=CC(C(C)(C)C)=CC=3)=CC=2)CCC(C)(C)C)=CC=1)=O>C1(C)C=CC=CC=1.O.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:30])[CH2:4][CH2:5][NH:6][C:7](=[O:29])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]([O:21][C:22]2[CH:23]=[N:24][C:25]([C:38]3[CH:39]=[CH:40][C:35]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:36][CH:37]=3)=[CH:26][CH:27]=2)[CH2:15][CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:10][CH:9]=1

Participants

8

Reactant 4

HCID 522689Potassium FluorideHCID 27343204-tert-Butylphenylboronic acidHCID 67153586HCID 67153586, compoundHCID 86615985HCID 86615985, compound

Product 1

HCID 67153562HCID 67153562, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 22272177Toluene waterSolvent

Procedure

To a solution of 3-{4-[1-(6-chloro-pyridin-3-yloxy)-4,4-dimethyl-pentyl]-benzoylamino}-propionic acid methyl ester (84 mg, 0.19 mmol) in toluene:water (1:1) (2 mL) is added palladium tetrakis triphenylphosphine (22.47 mg, 0.1 mol %), 4-tert-butylphenylboronic acid (58 mg, 0.39 mmol). The reaction is purged with nitrogen and heated to reflux and the potassium fluoride (23 mg, 0.39 mmol) is added. The reaction is monitored by HPLC, and upon completion, allowed to cool to room temperature. The reaction is diluted with ethyl acetate and then Celite is added, followed by water. This mixture is then filtered through a pad of Celite. The solution is separated in a separatory funnel and the organic layer is washed with 0.1N sodium hydroxide, water, and brine. The organic layer is dried over anhydrous sodium sulfate and concentrated. The 5-(4-{1-[6-(4-tert-butyl-phenyl)-pyridin-3-yloxy]-4,4-dimethyl-pentyl}-phenyl)-5-oxo-pentanoic acid methyl ester (80 mg, 0.15 mmol) is purified by flash column chromatography.

Workup

  1. customThe reaction is purged with nitrogen
  2. temperatureheated
  3. temperatureto reflux
  4. additionCelite is added
  5. filtrationThis mixture is then filtered through a pad of Celite
  6. customThe solution is separated in a separatory funnel
  7. washthe organic layer is washed with 0.1N sodium hydroxide, water, and brine
  8. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-ee715d0fb41249d69e53251197b55eba
Source dataset
uspto-grants-2013_12
Patent number
US08609892B2

Reaction notes

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