Hydrogen Peroxide → HCID 178480148, compound

HRID 2216933Notes

Reaction equation

HRID 2216933 reaction equation
C[Si](C)(C1C=CC=CC=1)[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH:9]1[CH2:13][CH2:12][CH2:11][N:10]1[CH3:14].F.[K].OO.O.C([O-])([O-])=[O:28].[K+].[K+]>CO>[CH3:14][N:10]1[CH2:11][CH2:12][CH2:13][CH:9]1[C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:3]=1[OH:28]

Participants

7

Reactant 5

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 167426194-(Dimethylphenylsilanyl)-3-(1-methylpyrrolidin-2-yl)pyridineHCID 53443437Potassium fluoride, 99%, spray-dried

Product 1

HCID 178480148HCID 178480148, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of II (0.9 g, 3.2 mmol) in 10 mL of methanol was added potassium hydrogen fluoride (0.25 g, 3.2 mmol). A solution of 30% hydrogen peroxide in water (0.88 mL, 7.7 mmol) was slowly added, and the reaction mixture was stirred and heated at 55° C. for 8 h. To the crude mixture was added K2CO3 until the pH of the solution became slightly basic (pH 8–9). After filtration of the solid and evaporation of the solvent, the crude product was purified by radial PLC (EtOAc) to yield 82% of III as a white solid. IR (neat) 2598, 23448, 1643 cm−1; 1H NMR (300 MHz, CDCl3) δ 8.68 (s, 1H), 8.58–8.56 (m, 1H), 8.12 (dd, 1H, J=1.5 and 8 Hz), 7.47 (dd, 1H, J=5.1 ans 8 Hz), 4.61 (dd, 1H, J=7.2 and 12 Hz), 3.79–3.59 (m, 2H), 2.94 (s, 3H), 2.72–2.1 (m, 4H); 13C NMR (75 MHz, CD3OD) δ 170.5, 152.8, 151.4, 141.3, 124.9, 78.3, 71.4, 54.1, 29.5, 21.1. HRMS Calcd for C10H14N2O: 179.1184. Found: 179.1190 [M+H]+. [α]D25: +23.8 (c=0.8, MeOH). IR (neat) 2598, 23448, 1643 cm−1, 1H NMR (300 MHz,) δ 8.68 (s, 1H), 8.58–8.56 (m, 1H), 8.12 (dd, 1H, J=1.5 and 8 Hz), 7.47 (dd, 1H, J=5.1 ans 8 Hz), 4.61 (dd, 1H, J=7.2 and 12 Hz), 3.79–3.59 (m, 2H), 2.94 (s, 3H), 2.72–2.1 (m, 4H); 13C NMR (75 MHz, CD3OD) δ 170.5, 152.8, 151.4, 141.3, 124.9, 78.3, 71.4, 54.1, 29.5, 21.1. HRMS Calcd for C10H14N2O: 179.1184. Found: 179.1190 [M+H]+. [α]D25+23.8 (c 8, MeOH).

Workup

  1. filtrationAfter filtration of the solid and evaporation of the solvent
  2. customthe crude product was purified by radial PLC (EtOAc)

Sources & evidence

ORD record
ord-22ba499cd0e34aefb062dbdc5c50e8f9
Source dataset
uspto-grants-2006_09
Patent number
US07112678B2

Reaction notes

Loading…