Water → HCID 86613494, compound

HRID 29115Notes

Reaction equation

HRID 29115 reaction equation
[C:1]([NH:5][C:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=[N:8][C:7]=1[C:15]1[S:16][C:17]([C:20]#[C:21][Si](C)(C)C)=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].O>CO.C(Cl)Cl>[C:1]([NH:5][C:6]1[N:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=[N:8][C:7]=1[C:15]1[S:16][C:17]([C:20]#[CH:21])=[CH:18][CH:19]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 69317391Tert-butyl-[2-(5-trimethylsilanylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine

Product 1

HCID 86613494HCID 86613494, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

11.5 g (31.3 mmol) of tert-butyl-[2-(5-trimethylsilanylethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine were dissolved in a mixture of MeOH (230 ml) and DCM (50 ml) and combined with 431 mg (3.13 mmol) of potassium carbonate The reaction solution was stirred at RT for 30 min and then combined with water (200 ml). The mixture was then extracted with DCM and the organic phase was washed with water and dried over MgSO4. After filtration and evaporation under a vacuum, 9.0 g (30.5 mmol, 97%) of tert-butyl-[2-(5-ethynyl-thiophen-2-yl)-imidazo[1,2-a]pyridin-3-yl]-amine were obtained.

Workup

  1. extractionThe mixture was then extracted with DCM
  2. washthe organic phase was washed with water
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration and evaporation under a vacuum

Sources & evidence

ORD record
ord-6b8c438f44ce44e794d4f7af3baf8665
Source dataset
uspto-grants-2008_09
Patent number
US07420056B2

Reaction notes

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