Trifluoroacetic acid → 6-Bromo-2-phenylimidazo[1,2-A]pyridin-7-amine

HRID 2382739Notes

Reaction equation

HRID 2382739 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[C:20]([Br:21])=[CH:19][N:18]2[CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=[C:17]2[CH:16]=1)(C)(C)C>C(Cl)Cl>[Br:21][C:20]1[C:15]([NH2:14])=[CH:16][C:17]2[N:18]([CH:22]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:24]=2)[CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67041813(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-carbamic acid tert-butyl ester

Product 1

HCID 670419136-Bromo-2-phenylimidazo[1,2-A]pyridin-7-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (15 ml) was added to a solution of (6-bromo-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-carbamic acid tert-butyl ester (2.75 g, 7.1 mmol) in CH2Cl2 (15 ml), and the mixture was stirred at r.t. overnight. The mixture was then washed (water, 2×50 ml), dried (Na2SO4), and the solvent was evaporated to give a first crop of the desired product. The water layer was made alkaline by addition of NaOH (conc. 14 ml), and extracted with dichloromethane. The combined organic layers were dried (Na2SO4) and evaporated to give a second crop of the desired product. The combined crops (2.02 g, 99%) were used in the next step without further purification. MS (m/e)=288.0 [M+H+].

Workup

  1. washThe mixture was then washed (water, 2×50 ml)
  2. dry with materialdried (Na2SO4)
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-aa78d8b6dc174e30925f9e444a42bdaa
Source dataset
uspto-grants-2012_09
Patent number
US08263584B2

Reaction notes

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