Potassium Carbonate → 4-[4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenyl]-N-(3-trifluoromethyl-phenyl)-butyramide

HRID 1446675Notes

Reaction equation

HRID 1446675 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][C:18]([NH:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)=[O:19])=[CH:11][CH:10]=2)O1.[Cl:32][C:33]1[CH:38]=[CH:37][N:36]2[C:39](I)=[CH:40][N:41]=[C:35]2[CH:34]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.ClCCl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:32][C:33]1[CH:38]=[CH:37][N:36]2[C:39]([C:9]3[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:28])([F:29])[F:30])[CH:22]=4)=[O:19])=[CH:13][CH:14]=3)=[CH:40][N:41]=[C:35]2[CH:34]=1

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 574976977-Chloro-3-iodoimidazo[1,2-a]pyridineHCID 685460734-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-N-(3-trifluoromethyl-phenyl)-butyramide

Product 1

HCID 685428324-[4-(7-Chloro-imidazo[1,2-a]pyridin-3-yl)-phenyl]-N-(3-trifluoromethyl-phenyl)-butyramideYield 62.6%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Suspend 4-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-N-(3-trifluoromethyl-phenyl)-butyramide (0.47 g, 1.15 mmol), 7-chloro-3-iodo-imidazo[1,2-a]pyridine (0.29 g, 1.05 mmol) and solid potassium carbonate (0.48 g, 3.45 mmol) in dioxane (4 mL) and water (2 mL). Deoxygenate the reaction contents with nitrogen for 10 minutes at room temperature. Add trans-dichlorobis(triphenylphosphine)palladium (II) (22 mg, 0.03 mmol) to the reaction. Fit a reflux condenser and heat the reaction to 105° C. over the weekend. Cool the reaction, dilute with dichloromethane and filter through Celite®. Concentrate the filtrate and then chromatograph on silica, using 0-3% methanol/ethyl acetate, to yield the product (301 mg, 57%). MS(ES), m/z 458 (M+1).

Workup

  1. customDeoxygenate
  2. customthe reaction contents with nitrogen for 10 minutes at room temperature
  3. temperatureheat
  4. customthe reaction to 105° C. over the weekend
  5. temperatureCool
  6. customthe reaction
  7. filtrationfilter through Celite®
  8. concentrationConcentrate the filtrate

Sources & evidence

ORD record
ord-66b40ce91cb54be4a6ddfcea1e681aaa
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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