Methanol → HCID 21873934, compound

HRID 723394Notes

Reaction equation

HRID 723394 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:9]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][CH:7]=[CH:6][N:5]2[C:17]=1[CH3:18].C([Li])(C)(C)C.[C:24](Cl)(=[O:26])[CH3:25].CO>C(OCC)C.CCCCC>[C:24]([C:8]1[CH:7]=[CH:6][N:5]2[C:17]([CH3:18])=[C:2]([CH3:1])[N:3]=[C:4]2[C:9]=1[NH:10][C:11](=[O:16])[C:12]([CH3:14])([CH3:15])[CH3:13])(=[O:26])[CH3:25]

Participants

7

Reactant 4

HCID 887MethanolHCID 6367Acetyl chlorideHCID 21873970HCID 21873970, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 21873934HCID 21873934, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8003PentaneSolvent

Conditions

Temperature
-40 °C

Procedure

A vigorously stirred solution of 65.4 g of 2,3-dimethyl-8-pivaloylaminoimidazo[1,2-a]pyridine in 1.4 l of diethyl ether is treated dropwise at −78° C. under argon protective gas with 500 ml of a commercially available, 1.5 molar solution of t-butyllithium in n-pentane such that the temperature does not rise above −70° C. The mixture is then cooled to −90° C. in the course of 15 min and 54 ml of acetyl chloride are added dropwise to the dark-red suspension. The mixture is then allowed to warm to −40° C. (30 min), treated with 60 ml of methanol, the contents of the flask are poured onto 1 l of ice water and the aqueous phase is extracted three times with 150 ml of methylene chloride each time. The combined organic phases are washed three times with 100 ml of water each time, dried over sodium sulfate and the solvent is stripped off in vacuo. The residue is purified on silica gel (eluent: ethyl acetate/petroleum ether=3/7). 23.2 g of the title compound are obtained.

Workup

  1. customdoes not rise above −70° C
  2. additionare added dropwise to the dark-red suspension
  3. extractionthe aqueous phase is extracted three times with 150 ml of methylene chloride each time
  4. washThe combined organic phases are washed three times with 100 ml of water each time
  5. dry with materialdried over sodium sulfate
  6. customThe residue is purified on silica gel (eluent: ethyl acetate/petroleum ether=3/7)

Sources & evidence

ORD record
ord-684b3cf1765c45e1abb49b8a5c13aeaf
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

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