Methanol → HCID 70818317, compound

HRID 591041Notes

Reaction equation

HRID 591041 reaction equation
[C:1](Cl)(=[O:3])C.[N:5]1[C:6]([CH:14]([O:17][Si](C)(C)C)[C:15]#N)=[CH:7][N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=12.C[OH:23]>>[OH:17][CH:14]([C:6]1[N:5]=[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][N:8]2[CH:7]=1)[C:15]([O:3][CH3:1])=[O:23]

Participants

4

Reactant 3

HCID 887MethanolHCID 6367Acetyl chlorideHCID 70818461HCID 70818461, compound

Product 1

HCID 70818317HCID 70818317, compoundYield 80%

Procedure

Acetyl chloride (0.79 mL, 11.1 mmol) was added to anhydrous methanol (7 mL) at 0° C. under nitrogen atmosphere. The mixture was stirred for 10 minutes before adding 2-{imidazo[1,2-a]pyridin-2-yl}-2-[(trimethylsilyl)oxy]acetonitrile (25a) (227 mg, 0.93 mmol). The mixture was stirred 45 minutes at reflux then 1 hour at room temperature. The solution was concentrated in vacuo. The saturated solution of sodium hydrogencarbonate (10 mL) was added to the residue. The aqueous layer was extracted with dichloromethane (2×10 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide the desired ester (25b) (153 mg, 0.74 mmol, 80%) as a yellow solid which was used without further purification.

Workup

  1. stirringThe mixture was stirred 45 minutes
  2. temperatureat reflux
  3. custom1 hour
  4. customat room temperature
  5. concentrationThe solution was concentrated in vacuo
  6. additionThe saturated solution of sodium hydrogencarbonate (10 mL) was added to the residue
  7. extractionThe aqueous layer was extracted with dichloromethane (2×10 mL)
  8. dry with materialThe organic layer was dried over sodium sulfate
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9731d2683f774f07bbef6ee010b7774d
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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