3-Cyanophenylboronic acid → HCID 67194524, compound

HRID 551267Notes

Reaction equation

HRID 551267 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].C(OC([N:19]1[CH2:24][CH:23]=[C:22](OS(C(F)(F)F)(=O)=O)[CH2:21][CH2:20]1)=O)(C)(C)C>C(#N)C.C(=O)([O-])[O-].[Na+].[Na+]>[NH:19]1[CH2:20][CH:21]=[C:22]([C:5]2[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=2)[C:1]#[N:2])[CH2:23][CH2:24]1

Participants

5

Reactant 2

HCID 27343253-Cyanophenylboronic acidHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 67194524HCID 67194524, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 10340Sodium CarbonateSolvent

Procedure

3-Cyanophenyl boronic acid (3.0 g, 20.4 mmol) and 4-(trifluoromethanesulfonyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (7.0 g, 21.1 mmol) are dissolved in acetonitrile (100 ml) and 0.4 M aqueous sodium carbonate (100 ml). The solution is degassed and treated with palladium tetrakistriphenylphosphine (1.2 g, 1.04 mmol) at 90° C. for 1 hour. The reaction is cooled, filtered and the filtrate is concentrated to an oil. The oil is extracted with methylene chloride (3×) and the solvent is removed under vacuum. The residue is chromatographed (15% ethyl acetate/hexane) to give the title compound as a white solid (6.0 g, 21.1 mmol). This material is treated with methylene chloride (100 ml) and 40% TFA/methylene chloride (100 ml) at ambient temperature for 2 h. The solvents are removed under vacuum and the residue is chromatographed (NH4OH/MeOH/CH2Cl2, 1:5:94) to give title compound as a brown solid contaminated with inorganic salts (4.6 g).1H NMR (CDCl3, 300 MHz) δ7.87 (s, 1H), 7.80 (d, 1H), 7.70 (d, 1H), 7.58 (t, 1H), 6,28 (m, 1H), 3.90 (m, 2H), 3.49 (t, 2H), 2.83 (m, 2H). EI MS M+ 184.

Workup

  1. customThe solution is degassed
  2. temperatureThe reaction is cooled
  3. filtrationfiltered
  4. concentrationthe filtrate is concentrated to an oil
  5. extractionThe oil is extracted with methylene chloride (3×)
  6. customthe solvent is removed under vacuum
  7. customThe residue is chromatographed (15% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-c8bedc8c433847d7ad70beadcee23dc0
Source dataset
uspto-grants-2011_05
Patent number
US07947684B2

Reaction notes

Loading…