Triethylamine → HCID 68877372, compound

HRID 1929889Notes

Reaction equation

HRID 1929889 reaction equation
[CH:1]1([C@:4]([OH:24])([CH3:23])[CH2:5][NH:6][C:7]([C:9]2[CH:14]=[N:13][C:12](Br)=[C:11]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:10]=2)=[O:8])[CH2:3][CH2:2]1.[CH2:25]([SiH:27]([CH2:30][CH3:31])[CH2:28][CH3:29])[CH3:26].[CH2:32](N(CC)CC)[CH3:33]>[Cu](I)I>[CH:1]1([C@:4]([OH:24])([CH3:23])[CH2:5][NH:6][C:7]([C:9]2[CH:14]=[N:13][C:12]([C:26]#[C:25][Si:27]([CH2:32][CH3:33])([CH2:30][CH3:31])[CH2:28][CH3:29])=[C:11]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)[N:10]=2)=[O:8])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12052TriethylsilaneHCID 86616978HCID 86616978, compound

Product 1

HCID 68877372HCID 68877372, compound

Reagents, catalysts & solvents 1

HCID 83717Copper iodideCatalyst

Procedure

A mixture of 7.0 mg bistriphenylphosphinpalladium dichloride and 4 mg copperiodide in 5 ml triethylamine was heated to reflux for 30 min. To the resulting solution was added 0.41 g 5-bromo-6-(4-chloro-phenyl)-pyrazine-2-carboxylic acid ((R)-2-cyclopropyl-2-hydroxy-propyl)-amide (example 62 a) and 0.28 g triethylsilane and the mixture was refluxed for 0.5 h. The reaction mixture was cooled to room temperature and partitioned between 10% citric acid and ethyl acetate. The organic phase was purified by chromatography on silica gel with heptane:ethyl acetate=1:1 to yield 0.45 g of 6-(4-chloro-phenyl)-5-triethylsilanylethynyl-pyrazine-2-carboxylic acid ((R)-2-cyclopropyl-2-hydroxy-propyl)-amide as a solidifying foam.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 min
  3. temperaturethe mixture was refluxed for 0.5 h
  4. custompartitioned between 10% citric acid and ethyl acetate
  5. customThe organic phase was purified by chromatography on silica gel with heptane

Sources & evidence

ORD record
ord-988548d9909348ea84f0b3a10a6c43db
Source dataset
uspto-grants-2012_05
Patent number
US08188093B2

Reaction notes

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