Hydrochloric Acid → Methyl 5-ethyl-6-(2-(hydroxymethyl)imidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate

HRID 1481704Notes

Reaction equation

HRID 1481704 reaction equation
[Si]([O:8][CH2:9][C:10]1[N:11]=[C:12]2[CH:17]=[CH:16][C:15]([C:18]3[C:27]([CH2:28][CH3:29])=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[C:20]([O:30][CH3:31])[N:19]=3)=[CH:14][N:13]2[CH:32]=1)(C(C)(C)C)(C)C.Cl>CO>[CH2:28]([C:27]1[C:18]([C:15]2[CH:16]=[CH:17][C:12]3[N:13]([CH:32]=[C:10]([CH2:9][OH:8])[N:11]=3)[CH:14]=2)=[N:19][C:20]([O:30][CH3:31])=[C:21]([CH:26]=1)[C:22]([O:24][CH3:25])=[O:23])[CH3:29]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71284421Methyl 6-(2-((tert-butyldimethylsilyloxy)methyl)imidazo[1,2-a]pyridin-6-yl)-5-ethyl-2-methoxynicotinate

Product 1

HCID 71284396Methyl 5-ethyl-6-(2-(hydroxymethyl)imidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinateYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To solution of methyl 6-(2-((tert-butyldimethylsilyloxy)methyl)imidazo[1,2-a]pyridin-6-yl)-5-ethyl-2-methoxynicotinate (0.911 g, 2.00 mmol) in MeOH (8 mL) was added 1M HCl (aqueous, 3.0 mL, 3.0 mmol). Reaction mixture was stirred at room temperature until starting material was completely consumed according to LC/MS. After ˜2 h MeOH was concentrated and residue was treated with NaHCO3 solution (aqueous saturated, 10 mL). Product was extracted with DCM (3×20 mL). Organic phase was washed with NaCl (aqueous saturated, 20 mL) and dried over Na2SO4. Removal of the solvent afforded methyl 5-ethyl-6-(2-(hydroxymethyl)imidazo[1,2-a]pyridin-6-yl)-2-methoxynicotinate (0.650 g) in 95% yield.

Workup

  1. customReaction mixture
  2. customwas completely consumed
  3. concentrationAfter ˜2 h MeOH was concentrated
  4. additionresidue was treated with NaHCO3 solution (aqueous saturated, 10 mL)
  5. extractionProduct was extracted with DCM (3×20 mL)
  6. washOrganic phase was washed with NaCl (aqueous saturated, 20 mL)
  7. dry with materialdried over Na2SO4
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-d9ecf39148a944cb9df6cbae1ba93c26
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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