Water → 2-(4-tert-Butylphenyl)-4-pyridinyl 4,4,4-trifluoro-1-butanesulfonate

HRID 896836Notes

Reaction equation

HRID 896836 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:14][C:15]([F:38])([F:37])[CH2:16][CH2:17][CH2:18][S:19]([O:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25](OS(C(F)(F)F)(=O)=O)[CH:24]=1)(=[O:21])=[O:20].C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1.C1([Pd-4](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:38][C:15]([F:14])([F:37])[CH2:16][CH2:17][CH2:18][S:19]([O:22][C:23]1[CH:24]=[CH:25][N:26]=[C:27]([C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=2)[CH:28]=1)(=[O:21])=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 27343204-tert-Butylphenylboronic acidHCID 208165222-Trifluoromethylsulfonyloxy-4-pyridinyl 4,4,4-trifluoro-1-butanesulfonate

Product 1

HCID 208164882-(4-tert-Butylphenyl)-4-pyridinyl 4,4,4-trifluoro-1-butanesulfonate

Reagents, catalysts & solvents 2

HCID 178420550HCID 178420550, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

42.2 mg (0.24 mmol) of 4-tert-butylbenzeneboronic acid, 90 mg (0.22 mmol) of 2-trifluoromethylsulfonyloxy-4-pyridinyl 4,4,4-trifluoro-1-butanesulfonate (Example 40A), 12.5 mg (0.01 mmol) of tetrakisphenylpalladium(0) and 68.6 mg (0.65 mmol) of sodium carbonate are heated in 5 ml of dioxane at 80° C. under argon for 2 hours. The reaction mixture is cooled, mixed with 0.5 ml of water and filtered through a cartridge packed with 3 g of Extrelut NT3 (Merck) and thoroughly washed with dichloromethane, and the solvent is distilled off under reduced pressure. The residue is purified by preparative HPLC and chromatography on silica gel (toluene).

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationfiltered through a cartridge
  3. washthoroughly washed with dichloromethane
  4. distillationthe solvent is distilled off under reduced pressure
  5. customThe residue is purified by preparative HPLC and chromatography on silica gel (toluene)

Sources & evidence

ORD record
ord-a4ee7a007203496c91001fd7543136de
Source dataset
uspto-grants-2005_07
Patent number
US06919470B2

Reaction notes

Loading…