Triethylamine → 2-Oxo-1-(4-(trifluoromethoxy)phenyl)-1,2-dihydropyridine-3-carbaldehyde

HRID 874687Notes

Reaction equation

HRID 874687 reaction equation
[O:1]=[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][NH:3]1.[F:10][C:11]([F:23])([F:22])[O:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.CCN(CC)CC>CC([O-])=O.CC([O-])=O.[Cu+2].CS(C)=O>[O:1]=[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][CH:5]=[CH:4][N:3]1[C:16]1[CH:15]=[CH:14][C:13]([O:12][C:11]([F:10])([F:22])[F:23])=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 70621962-Oxo-1,2-dihydropyridine-3-carbaldehyde

Product 1

HCID 895362582-Oxo-1-(4-(trifluoromethoxy)phenyl)-1,2-dihydropyridine-3-carbaldehydeYield 25%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

In a microwave vial were placed 2-oxo-1,2-dihydropyridine-3-carbaldehyde 1-1 (200 mg, 1.62 mmol), 4-trifluoromethoxyphenylboronic acid 4-1 (660 mg, 3.25 mmol), and anhydrous Cu(OAc)2 (295 mg, 1.62 mmol). To the mixture was added DMSO (3.20 mL) followed by Et3N (0.45 mL, 3.25 mmol). The mixture was irradiated in microwave apparatus (Biotage) at 100° C. for 15 minutes and cooled to room temperature. The mixture was concentrated and the residue was purified by silica gel chromatography (0-20% EtOAc in hexane) to give 105 mg (25%) of 2-2 as a pale yellow solid: 1H NMR (300 MHz, CDCl3) δ 10.34 (1H, s), 8.13 (1H, dd, J=6.9, 2.1 Hz), 7.63 (1H, dd, J=6.9, 2.1 Hz), 7.47-7.36 (4H, m), 6.44 (1H, t, J=6.9 Hz); ESI-MS m/z 284 [C13H8F3NO3+H]+.

Workup

  1. customThe mixture was irradiated in microwave apparatus (Biotage) at 100° C. for 15 minutes
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by silica gel chromatography (0-20% EtOAc in hexane)

Sources & evidence

ORD record
ord-56a71d5dd9314f2e9b2f31cbf809dc5c
Source dataset
uspto-grants-2015_03
Patent number
US08980916B2

Reaction notes

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