6-Tert-butyl 2-ethyl 5-chloro-7-methylimidazo[1,2-a]pyridine-2,6-dicarboxylate → 5-Chloro-2-(ethoxycarbonyl)-7-methylimidazo[1,2-a]pyridine-6-carboxylic acid

HRID 1481962Notes

Reaction equation

HRID 1481962 reaction equation
[Cl:1][C:2]1[N:7]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=[C:6]2[CH:5]=[C:4]([CH3:16])[C:3]=1[C:17]([O:19]C(C)(C)C)=[O:18]>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[N:7]2[CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=[C:6]2[CH:5]=[C:4]([CH3:16])[C:3]=1[C:17]([OH:19])=[O:18]

Participants

3

Reactant 1

HCID 1176324636-Tert-butyl 2-ethyl 5-chloro-7-methylimidazo[1,2-a]pyridine-2,6-dicarboxylate

Product 1

HCID 1176324075-Chloro-2-(ethoxycarbonyl)-7-methylimidazo[1,2-a]pyridine-6-carboxylic acidYield 140.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

6-tert-butyl 2-ethyl 5-chloro-7-methylimidazo[1,2-a]pyridine-2,6-dicarboxylate (11.4 g, 27.2 mmol, 1 equiv) was treated with TFA (100 mL) and stirred for 2 h. Upon completion, the reaction was concentrated in vacuo. The crude product was triturated in ether and filtered to provide the product (10.8 g, 100%) as a cream colored solid. LCMS (ESI, M+1): 283.1.

Workup

  1. concentrationUpon completion, the reaction was concentrated in vacuo
  2. customThe crude product was triturated in ether
  3. filtrationfiltered

Sources & evidence

ORD record
ord-87d0e33a5fb3483e9ba1a178ca3411c2
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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