Potassium Fluoride → HCID 59355967, compound

HRID 660995Notes

Reaction equation

HRID 660995 reaction equation
[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[S:10][C:11]([CH:14]([O:21][C:22]2[CH:27]=[C:26]([CH3:28])[C:25](I)=[C:24]([CH3:30])[CH:23]=2)[CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:13]=1)=[O:8].[CH:32]([C:35]1[CH:40]=[CH:39][C:38](B(O)O)=[CH:37][CH:36]=1)([CH3:34])[CH3:33].[F-].[K+]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[S:10][C:11]([CH:14]([O:21][C:22]2[CH:27]=[C:26]([CH3:28])[C:25]([C:38]3[CH:39]=[CH:40][C:35]([CH:32]([CH3:34])[CH3:33])=[CH:36][CH:37]=3)=[C:24]([CH3:30])[CH:23]=2)[CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:13]=1)=[O:8]

Participants

5

Reactant 3

HCID 522689Potassium FluorideHCID 27734804-Isopropylphenylboronic acidHCID 59355941HCID 59355941, compound

Product 1

HCID 59355967HCID 59355967, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-({5-[4,4,4-Trifluoro-1-(4-iodo-3,5-dimethyl-phenoxy)-butyl]-thiophene-2-carbonyl}-amino)-propionic acid methyl ester (300 mg, 0.53 mmol) was dissolved in toluene (1.5 mL), followed by palladium tetrakis triphenylphosphine (30 mg, 0.03 mmol), 4-isopropyl-phenyl boronic acid (173 mg, 1.05 mmol), and potassium fluoride (61.2 mg, 1.05 mmol). The reaction was purged with nitrogen and heated to reflux, then water (1.5 mL) was added. The reaction was monitored by HPLC, and upon completion, allowed to cool to room temperature. The reaction was diluted with EtOAc and then Celite® added, followed by water. This mixture was then filtered through a pad of Celite®. The solution was separated in a separatory funnel and the organic layer was washed with 0.1N sodium hydroxide, water, and brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The product was purified by flash column chromatography (225 mg). MS(ES): 562.3 [M+H]+.

Workup

  1. customThe reaction was purged with nitrogen
  2. temperatureheated
  3. temperatureto reflux
  4. additionwater (1.5 mL) was added
  5. additionThe reaction was diluted with EtOAc
  6. additionCelite® added
  7. filtrationThis mixture was then filtered through a pad of Celite®
  8. customThe solution was separated in a separatory funnel
  9. washthe organic layer was washed with 0.1N sodium hydroxide, water, and brine
  10. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  11. concentrationconcentrated
  12. customThe product was purified by flash column chromatography (225 mg)

Sources & evidence

ORD record
ord-107a2a08a6c24b22bda2418276e73986
Source dataset
uspto-grants-2011_12
Patent number
US08084489B2

Reaction notes

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