Potassium Carbonate → HCID 89648349, compound

HRID 929449Notes

Reaction equation

HRID 929449 reaction equation
[CH3:1][C:2]([C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)([CH2:4][CH2:5][CH3:6])[CH3:3].Cl[C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[CH3:1][C:2]([C:7]1[CH:8]=[CH:9][C:10]([O:13][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][N:16]=2)=[CH:11][CH:12]=1)([CH2:4][CH2:5][CH3:6])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 217236544-(2-Methylpentan-2-yl)phenol

Product 1

HCID 89648349HCID 89648349, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Following procedure A, 4-(2-methylpentan-2-yl)phenol (52 mg, 0.29 mmol, 1.00 eq) and 2-chloro-5-nitropyridine (57 mg, 0.36 mmol, 1.23 eq) were dissolved in DMSO (6 mL). Anhydrous K2CO3 (66 mg, 0.48 mmol, 1.65 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 1:50) to afford the title compound as colourless solid (86 mg, 0.29 mmol, 98% yield). Rf=0.50 (EtOAc/PE 1:10). HRMS (ESI) calcd. for C17H21N2O3+ [M+H]+ 301.1547. found: 301.1545. 1H NMR (400 MHz, CDCl3) δ 9.07 (d, J=2.7 Hz, 1H, aromatic H), 8.46 (dd, J=9.1, 2.8 Hz, 1H, aromatic H), 7.45-7.35 (m, 2H, aromatic H), 7.14-7.05 (m, 2H, aromatic H), 6.99 (dd, J=9.0, 0.6 Hz, 1H, aromatic H), 1.65-1.54 (m, 2H, C(CH3)2CH2CH2CH3), 1.32 (s, 6H, C(CH3)2CH2CH2CH3), 1.19-1.05 (m, 2H, C(CH3)2CH2CH2CH3), 0.84 (t, J=7.3 Hz, 3H, C(CH3)2CH2CH2CH3). 13C NMR (101 MHz, CDCl3) δ 167.17, 150.43, 147.69, 145.21, 140.26, 134.90, 127.44, 120.72, 111.29, 47.27, 37.74, 29.07, 18.08, 14.87.

Workup

  1. extractionAfter extraction with Et2O
  2. customthe crude product was purified by flash column chromatography (SiO2; EtOAc/petrolether 1:50)

Sources & evidence

ORD record
ord-635370a2e1d74e3da2499cfb572193f4
Source dataset
uspto-grants-2016_03
Patent number
US09296682B2

Reaction notes

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