Acetic Acid → 4-[4-(Diethoxyphosphorylmethylsulfonyl)piperazin-1-yl]-2-methyl-quinoline

HRID 333933Notes

Reaction equation

[CH3:1][C:2]1[CH:11]=[C:10]([N:12]2[CH2:17][CH2:16][N:15]([S:18]([CH3:21])(=[O:20])=[O:19])[CH2:14][CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[CH2:32]([O:34][P:35](Cl)([O:37][CH2:38][CH3:39])=[O:36])[CH3:33].C(O)(=O)C>C1COCC1.O>[CH2:32]([O:34][P:35]([CH2:21][S:18]([N:15]1[CH2:14][CH2:13][N:12]([C:10]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=[C:2]([CH3:1])[CH:11]=2)[CH2:17][CH2:16]1)(=[O:20])=[O:19])([O:37][CH2:38][CH3:39])=[O:36])[CH3:33]

Participants

Conditions

Temperature: -78 °C

Procedure

2-Methyl-4-(4-methylsulfonylpiperazin-1-yl)quinoline (70 mg, 0.23 mmol) was placed in a Schlenk tube under an argon atmosphere, anhydrous THF (1.5 ml) was added and the solution cooled to −78° C. Lithium hexamethyldisilazid (50.6 mmol, 50.6 μl of a 1M solution in anhydrous THF) was added dropwise and the mixture stirred for one hour at −78° C. Diethylchlorophosphate (33.3 μl, 0.23 mmol) was added dropwise and stirring was continued for one hour. Acetic acid (100 μl) and water (1.5 ml) were added, the temperature raised slowly to room temperature and the mixture was extracted with diethylether (3×). The combined organic phases were washed with water and brine and evaporated to dryness under reduced pressure. 99 mg of an oily residue were obtained (0.22 mmol, 98%). MS (APCI) m/z=441.7 [M+1]+.

Workup

stirringstirring
waitwas continued for one hour
temperaturethe temperature raised slowly to room temperature
extractionthe mixture was extracted with diethylether (3×)
washThe combined organic phases were washed with water and brine
customevaporated to dryness under reduced pressure

Sources & evidence

ORD record: ord-aabd939b1fc54fb99154219a2c342035
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883791B2

Reaction notes

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