Triethylamine → HCID 23502795, compound

HRID 1835348Notes

Reaction equation

HRID 1835348 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12](I)=[N:11][CH:10]=1.C(N(CC)CC)C.[CH3:41][Si:42]([C:45]#[CH:46])([CH3:44])[CH3:43]>O1CCCC1.COC(C)(C)C.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.[Cu]I>[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[CH2:6][N:7]([CH3:24])[C:8](=[O:23])[C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:21])=[CH:13][C:12]([C:46]#[C:45][Si:42]([CH3:44])([CH3:43])[CH3:41])=[N:11][CH:10]=1

Participants

8

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 10231844N-(3,5-Bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide

Product 1

HCID 23502795HCID 23502795, compoundYield 83.2%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

To a mixture of 200 mg (0.346 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-6-iodo-N-methyl-4-o-tolyl-nicotinamide (Example 4), 0.073 ml (0.52 mmol) triethylamine, 5 mg (0.007 mmol) bis(triphenylphosphine)palladium(II) chloride and 3 mg (0.014 mmol) copper(I) iodide in 1 ml tetrahydrofuran a solution of 0.098 ml (0.69 mmol) trimethylsilylacetylene in 0.5 ml tetrahydrofuran was added at room temperature. After stirring for 17 h the mixture was diluted with tert-butyl methyl ether. Washing with a saturated aqueous solution of ammonium chloride was followed by drying with sodium sulfate and evaporation of the solvent. Column chromatography afforded 158 mg (83%) of the title compound as a light brown solid.

Workup

  1. additionwas added at room temperature
  2. washWashing with a saturated aqueous solution of ammonium chloride
  3. dry with materialby drying with sodium sulfate and evaporation of the solvent

Sources & evidence

ORD record
ord-1bcc6da4c75a4983827222989fef630d
Source dataset
uspto-grants-2004_08
Patent number
US06770637B2

Reaction notes

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