Ethanol → Ethyl 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylate

HRID 706599Notes

Reaction equation

HRID 706599 reaction equation
[CH3:1][C:2]1([CH3:16])[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)[CH2:4][O:3]1.C(O)C.Cl[CH:21]([CH:27]=O)[C:22]([O:24][CH2:25][CH3:26])=[O:23].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[CH3:1][C:2]1([CH3:16])[O:6][CH:5]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][N:12]3[C:21]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:27][N:15]=[C:11]3[CH:10]=2)[CH2:4][O:3]1

Participants

6

Reactant 4

HCID 702EthanolHCID 118030Ethyl (chloroformyl)acetateHCID 516892Sodium BicarbonateHCID 509875954-((2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)pyridin-2-amine

Product 1

HCID 67259610Ethyl 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
60 °C

Procedure

4-((2,2-Dimethyl-1,3-dioxolan-4-yl)methoxy)pyridin-2-amine (5.6 g, 0.025 mol) was mixed with ethanol (60 mL) in a reaction flask under an atmosphere of dry nitrogen. A solution of ethyl 2-chloro-3-oxopropanoate (5% in benzene; 93 mL; Commercial solution from Toronto Research Chemicals Inc.) was added. The mixture was heated to 60° C. under nitrogen for 2 hours. After allowing the mixture to cool the solvent was removed under vacuum to give a brown solid. The solid was mixed with ethyl acetate (200 mL) and sodium bicarbonate solution (100 mL) and stirred to dissolve. The phases were separated and the bicarbonate solution was extracted further with ethyl acetate (50 mL). The combined ethyl acetate extracts were dried over sodium sulfate, filtered and concentrated under vacuum to give a solid. The crude material was dissolved in ethyl acetate and passed through a short column of silica gel, eluting with ethyl acetate to give ethyl 7-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)imidazo[1,2-a]pyridine-3-carboxylate as a pale yellow solid (5.76 g).

Workup

  1. temperatureto cool the solvent
  2. customwas removed under vacuum
  3. customto give a brown solid
  4. dissolutionto dissolve
  5. customThe phases were separated
  6. extractionthe bicarbonate solution was extracted further with ethyl acetate (50 mL)
  7. dry with materialThe combined ethyl acetate extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customto give a solid
  11. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-25645ffdb6d64a1db70459bad409b5d2
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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