2-Aminopyridine → [2-(5-Bromothiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine

HRID 29102

Reaction equation

HRID 29102 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:8][C:9]([N+:16]#[C-:17])([CH3:15])[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12].[Br:18][C:19]1[S:23][C:22]([CH:24]=O)=[CH:21][CH:20]=1.Cl(O)(=O)(=O)=O>C(Cl)Cl>[Br:18][C:19]1[S:23][C:22]([C:24]2[N:1]=[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]3[C:17]=2[NH:16][C:9]([CH3:15])([CH3:8])[CH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 104392-AminopyridineHCID 24247Perchloric AcidHCID 267251,1,3,3-Tetramethylbutyl isocyanideHCID 784285-Bromothiophene-2-carbaldehyde

Product 1

HCID 69317913[2-(5-Bromothiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amineYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

235 mg (2.5 mmol) of 2-aminopyridine were dissolved together with 0.42 ml (2.5 mmol) of 1,1,3,3-tetramethyl-butylisonitrile and 0.27 ml (2.5 mmol) of 5-bromothiophene-2-carbaldehyde in DCM (5 ml). After addition of perchloric acid (0.25 ml), the mixture was stirred at RT for 5 d. Washing was then performed with a sat. aq. sodium carbonate solution and a sat. aq. common salt solution. The organic phase was dried over magnesium sulfate, filtered and evaporated under a vacuum. After carrying out column chromatography (EA/DIPE/DCM 2:2:1) with the group, 724 mg (1.7 mmol, 71% of theoretical) of [2-(5-bromothiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-(1,1,3,3-tetramethyl-butyl)-amine were obtained.

Workup

  1. washWashing
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated under a vacuum

Sources & evidence

ORD record
ord-5240d8b45e85487baca690c674fe436e
Source dataset
uspto-grants-2008_09
Patent number
US07420056B2

Linked notes

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