Tetrahydrofuran → 6-(4-Formylphenyl)-5-phenylnicotinonitrile

HRID 2219070Notes

Reaction equation

HRID 2219070 reaction equation
FC(F)(F)S(O[C:7]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][C:10]([C:19]#[N:20])=[CH:9][N:8]=1)(=O)=O.[CH:23]([C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)=[O:24].C([O-])([O-])=O.[Cs+].[Cs+].O.C1COCC1>C(Cl)Cl>[CH:23]([C:25]1[CH:30]=[CH:29][C:28]([C:7]2[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][C:10]([C:19]#[N:20])=[CH:9][N:8]=2)=[CH:27][CH:26]=1)=[O:24]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 5910734-Formylphenylboronic AcidHCID 860085335-Cyano-3-phenylpyridin-2-yl trifluoromethanesulfonateHCID 86609353Cs2CO3 water

Product 1

HCID 860085356-(4-Formylphenyl)-5-phenylnicotinonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-cyano-3-phenylpyridin-2-yl trifluoromethanesulfonate (1-2; 328 mg, 1.0 mmol), 4-formylphenylboronic acid (225 mg, 1.5 mmol), Pd(dppf)(CH2Cl2) (16 mg, 0.02 mmol), 2 M of Cs2CO3 water solution (2 mL, 4 mmol), and THF (2 mL) was microwaved (Smith-Synthesizer) at 160° C. for 10 min. After cooled to rt, the reaction mixture was treated with DCM (40 mL) and washed with water, brine and dried over anhydrous Na2SO4. Filtration and concentration afforded the crude product which was purified by flash chromatography on silica gel to give pure 6-(4-formylphenyl)-5-phenylnicotinonitrile (1-3). Analytical LCMS: single peak (214 nm), 3.240 min. 1H NMR (500 MHz, CDCl3): δ 10.01(s, 1H), 8.92 (d, J=2.0 Hz, 1H), 8.04 (d, J=2.0 Hz, 1H), 7.79 (d, J=8.2 Hz, 2H), 7.55 (d, J=8.2 Hz, 1H), 7.31-7.39 (m, 3H), 7.13-7.18 (m, 2H).

Workup

  1. customwas microwaved (Smith-Synthesizer) at 160° C. for 10 min
  2. washwashed with water, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationFiltration and concentration
  5. customafforded the crude product which
  6. customwas purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-fbc5438eff56489dbcdf78d9e112b5b2
Source dataset
uspto-grants-2008_08
Patent number
US07414055B2

Reaction notes

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