Potassium Carbonate → 3-Ethynyl-8-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridine

HRID 269023Notes

Reaction equation

HRID 269023 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[C:4]2[N:5]([C:19]([C:22]#[C:23][Si](C)(C)C)=[CH:20][N:21]=2)[CH:6]=[C:7]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=2)[CH:8]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO.CC(OC)(C)C>[C:22]([C:19]1[N:5]2[CH:6]=[C:7]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([F:18])([F:17])[F:16])=[CH:11][CH:10]=3)[CH:8]=[C:3]([C:2]([F:1])([F:29])[F:28])[C:4]2=[N:21][CH:20]=1)#[CH:23]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 866080108-Trifluoromethyl-6-(4-trifluoromethyl-phenyl)-3-trimethylsilanylethynyl-imidazo[1,2-a]pyridine

Product 1

HCID 866080113-Ethynyl-8-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-imidazo[1,2-a]pyridineYield 66%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 8-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-3-trimethylsilanylethynyl-imidazo[1,2-a]pyridine (10.5 g, 25 mmol) in THF (100 mL) and MeOH (250 mL) at 0° C. was added K2CO3 (340 mg, 10 mol %) and the mixture was stirred at 0° C. for 6 h. Diluted with TBME and ice water, separated, washed with brine, dried over Na2SO4, totally evaporated. Purified by column chromatography (heptane/AcOEt) and trituration with heptane and filtration gave the product as an off-white solid (5.8 g, 66%). MS (ISP) 355.0 [(M+H)+].

Workup

  1. customseparated
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customtotally evaporated
  5. filtrationPurified by column chromatography (heptane/AcOEt) and trituration with heptane and filtration

Sources & evidence

ORD record
ord-485d693714d84f20958bbef1541a19b3
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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