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3-Cyanophenylboronic acid → tert-butyl 4-(3-cyanophenyl)-3,6-dihydropyridine-1(2H)-carboxylate

HRID 551269
Notes
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Reaction equation

HRID 551269 reaction equation
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH:23]=[C:22](OS(C(F)(F)F)(=O)=O)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13]>C(#N)C.C(=O)([O-])[O-].[Na+].[Na+]>[C:12]([O:16][C:17]([N:19]1[CH2:20][CH:21]=[C:22]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)[CH2:23][CH2:24]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

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

Product 1

HCID 51356836tert-butyl 4-(3-cyanophenyl)-3,6-dihydropyridine-1(2H)-carboxylateYield 77.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 10340
Sodium Carbonate
Solvent

Procedure

3-Cyanophenyl boronic acid (1.8 g, 12.2 mmol) and 4-(trifluoromethanesulfonyloxy)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (5.0 g, 15.2 mmol;) are dissolved in acetonitrile (60 ml) and 0.4 M aqueous sodium carbonate (60 ml). The solution is degassed and treated with palladium tetrakistriphenyl phosphine (0.81 g, 0.7 mmol) at 90° C. for 1 hour. The reaction is cooled, filtered warmed 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 (2.7 g, 9.5 mmol). 1H NMR (CDCl3, 300 MHz) δ 7.63 (s, 1H), 7.55 (m, 2H), 7.44 (t, 1H), 6.10 (br, 1H), 4.09 (m, 2H), 3.63 (t, 2H), 2.50 (br, 2H). EI MS M++1: 285.

Workup

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

Sources & evidence

ORD record
ord-a09f6e6a5fff4728ad70661fa982162d
Source dataset
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07947684B2

Reaction notes

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