tert-Butyl 2-(3-bromophenyl)-5-chloro-7,8-dimethylimidazo[1,2-a]pyridine-6-carboxylate → 2-(3-Bromophenyl)-5-chloro-7,8-dimethylimidazo[1,2-a]pyridine-6-carboxylic acid

HRID 1482063Notes

Reaction equation

HRID 1482063 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[C:14]([CH3:17])[C:13]([C:18]([O:20]C(C)(C)C)=[O:19])=[C:12]([Cl:25])[N:11]3[CH:26]=2)[CH:5]=[CH:6][CH:7]=1>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[C:14]([CH3:17])[C:13]([C:18]([OH:20])=[O:19])=[C:12]([Cl:25])[N:11]3[CH:26]=2)[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 1

HCID 118308922tert-Butyl 2-(3-bromophenyl)-5-chloro-7,8-dimethylimidazo[1,2-a]pyridine-6-carboxylate

Product 1

HCID 1183087932-(3-Bromophenyl)-5-chloro-7,8-dimethylimidazo[1,2-a]pyridine-6-carboxylic acidYield 80.2%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 2-(3-bromophenyl)-5-chloro-7,8-dimethylimidazo[1,2-a]pyridine-6-carboxylate (1 g, 2.30 mmol, 1 equiv) in TFA (5 mL) was stirred 3 h. The reaction mixture was then concentrated in vacuo and the residue was triturated with ether. The solid was filtered and washed with ether to provide the product (0.70 g, 80%). LCMS (ESI, M+1): 379.0.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was triturated with ether
  3. filtrationThe solid was filtered
  4. washwashed with ether

Sources & evidence

ORD record
ord-bb9d9de4e4d7411bb28866970c2cacc2
Source dataset
uspto-grants-2016_08
Patent number
US09409922B2

Reaction notes

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