Potassium Carbonate → HCID 31244404, compound

HRID 929445Notes

Reaction equation

HRID 929445 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[C:11]([C:15]1[CH:16]=[C:17]([OH:21])[CH:18]=[CH:19][CH:20]=1)([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[C:11]([C:15]1[CH:16]=[C:17]([CH:18]=[CH:19][CH:20]=1)[O:21][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1)([CH3:14])([CH3:12])[CH3:13]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 783082-Chloro-5-nitropyridine

Product 1

HCID 31244404HCID 31244404, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following procedure A, 2-chloro-5-nitropyridine (300 mg, 1.89 mmol, 1.00 eq) and 3-tert-butylphenol (358 mg, 2.38 mmol, 1.26 eq) were dissolved in DMSO (6 mL). Anhydrous K2CO3 (420 mg, 3.04 mmol, 1.60 eq) was added and the reaction mixture was stirred at room temperature for 70 h. After extraction with Et2O, the crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:100) to afford the title compound as colourless solid (512 mg, 1.88 mmol, 99% yield). Rf=0.37 (EtOAc/PE 1:20). HRMS (ESI) calcd. for C15H17N2O3+ [M+H]+ 273.1234. found: 273.1232. 1H NMR (400 MHz, CDCl3) δ 9.08-9.04 (m, 2H, aromatic H), 8.47 (dd, J=9.1, 2.8 Hz, 1H, aromatic H), 7.39 (t, J=7.9 Hz, 1H, aromatic H), 7.33 (ddd, J=7.9, 1.8, 1.2 Hz, 1H, aromatic H), 7.17 (t, J=2.1 Hz, 1H, aromatic H), 7.01 (dd, J=9.1, 0.5 Hz, 1H, aromatic H), 6.98 (ddd, J=7.9, 2.4, 1.2 Hz, 1H, aromatic H), 1.34 (s, 9H, C(CH3)3). 13C NMR (101 MHz, CDCl3) δ 167.21, 153.88, 152.76, 145.26, 140.31, 134.93, 129.50, 123.17, 118.62, 118.47, 111.28, 35.02, 31.36.

Workup

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

Sources & evidence

ORD record
ord-fc0087330fe14799afa7b1c69eaa1c56
Source dataset
uspto-grants-2016_03
Patent number
US09296682B2

Reaction notes

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