Potassium Carbonate → HCID 89648549, compound

HRID 929439Notes

Reaction equation

HRID 929439 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH:11]1([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH:11]1([C:17]2[CH:18]=[CH:19][C:20]([O:23][C:2]3[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=3)=[CH:21][CH:22]=2)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 143274-CyclohexylphenolHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 89648549HCID 89648549, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following procedure A, 2-chloro-5-nitropyridine (300 mg, 1.89 mmol, 1.00 eq) and 4-cyclohexylphenol (417 mg, 2.37 mmol, 1.25 eq) were dissolved in DMSO (6 mL). Anhydrous K2CO3 (397 mg, 2.87 mmol, 1.52 eq) was added and the reaction mixture was stirred at room temperature for 27 h. After extraction with Et2O, the crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:100 to 1:75) to afford the title compound as colourless solid (600 mg, 2.01 mmol, quant. yield). Rf=0.35 (EtOAc/PE 1:20). HRMS (ESI) calcd. for C17H19N2O3+ [M+H]+ 299.1390. found: 299.1392. 1H NMR (400 MHz, CDCl3) δ 9.06 (d, J=2.9 Hz, 1H, aromatic H), 8.46 (dd, J=9.1, 2.9 Hz, 1H, aromatic H), 7.31-7.22 (m, 2H, aromatic H), 7.07 (dd, J=8.7, 2.3 Hz, 2H, aromatic H), 7.00 (d, J=9.1 Hz, 1H, aromatic H), 2.58-2.51 (m, 1H, cyclohexyl H), 2.01-1.64 (m, 5H, cyclohexyl H), 1.56-1.10 (m, 5H, cyclohexyl H). 13C NMR (101 MHz, CDCl3) δ 167.18, 150.71, 145.88, 145.17, 140.22, 134.89, 128.30, 121.12, 111.30, 44.08, 34.59, 26.95, 26.19.

Workup

  1. extractionAfter extraction with Et2O
  2. customthe crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:100 to 1:75)

Sources & evidence

ORD record
ord-f5ab67be51404f03be134bf285e7179c
Source dataset
uspto-grants-2016_03
Patent number
US09296682B2

Reaction notes

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