Iodopyrazine → HCID 57815307, compound

HRID 385575Notes

Reaction equation

HRID 385575 reaction equation
[CH2:1]([N:4]([CH:12]1[CH2:17][CH2:16][N:15]([C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:14][CH2:13]1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[C:2]#[CH:3].I[C:25]1[CH:30]=[N:29][CH:28]=[CH:27][N:26]=1>C(N(CC)CC)C.[Cu]I.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>[N:26]1[CH:27]=[CH:28][N:29]=[CH:30][C:25]=1[C:3]#[C:2][CH2:1][N:4]([CH:12]1[CH2:13][CH2:14][N:15]([C:18](=[O:23])[C:19]([F:20])([F:21])[F:22])[CH2:16][CH2:17]1)[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 2

HCID 642841IodopyrazineHCID 57815383HCID 57815383, compound

Product 1

HCID 57815307HCID 57815307, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of 0.20 g of tert-butyl (2-propyn-1-yl)(1-(trifluoroacetyl)piperidin-4-yl)carbamate in 6.0 mL of triethylamine, 59 μL of iodopyrazine, 0.57 mg of copper (I) iodide, and 4.2 mg of dichlorobis(triphenylphosphine)palladium(II) were added under a nitrogen atmosphere, and the mixture was stirred at 60 to 70° C. for 4 hours 30 minutes. The insoluble substance was filtered off, and the solvent was distilled off under reduced pressure. The resultant residue was purified by flash silica gel column chromatography using gradient elution with hexane:ethyl acetate=60:40 to 50:50 to obtain 0.17 g of tert-butyl (3-(pyrazin-2-yl)-2-propyn-1-yl)(1-(trifluoroacetyl)piperidin-4-yl)carbamate as a colorless oily substance.

Workup

  1. filtrationThe insoluble substance was filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. customThe resultant residue was purified by flash silica gel column chromatography
  4. washelution with hexane

Sources & evidence

ORD record
ord-cacd2ab473c54e86911c53c19d366b03
Source dataset
uspto-grants-2013_02
Patent number
US08367831B2

Reaction notes

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