Triethylamine → HCID 86717497, compound

HRID 712043Notes

Reaction equation

HRID 712043 reaction equation
Br[C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH:9]=[C:10]([CH3:12])[N:11]=2)[C:7]=1[Cl:8].[CH3:13][Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15].C(N(CC)CC)C>CN(C)C=O.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>[Cl:8][C:7]1[N:6]2[CH:9]=[C:10]([CH3:12])[N:11]=[C:5]2[CH:4]=[N:3][C:2]=1[C:18]#[C:17][Si:14]([CH3:16])([CH3:15])[CH3:13]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 86717496HCID 86717496, compound

Product 1

HCID 86717497HCID 86717497, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
45 °C

Procedure

A mixture of 6-bromo-5-chloro-2-methylimidazo[1,2-a]pyrazine (0.710 g, 2.88 mmol), bis(triphenylphosphine)palladium(II) chloride (0.1 g, 0.1 mmol), (trimethylsilyl)acetylene (0.90 mL, 6.3 mmol), copper(I) iodide (0.04 g, 0.2 mmol), and triethylamine (0.803 mL, 5.76 mmol) in N,N-dimethylformamide (8.5 mL) was heated in an oil bath at 45° C. and stirring for 14 h. The reaction was quenched with water (20 ml) and was extracted with ethyl acetate (2×100 ml). The combined organic extracts were washed with water (10 ml), saturated NaCl (10 ml), dried over Na2SO4 and the solvent removed in vacuo. The product was purified by silica gel chromatography eluting with 10-20% EtOAc in hexanes to give the desired product (0.39 g, 76%). LCMS calculated for C12H15ClN3Si (M+H)+: m/z=264.1. Found: 264.0.

Workup

  1. customThe reaction was quenched with water (20 ml)
  2. extractionwas extracted with ethyl acetate (2×100 ml)
  3. washThe combined organic extracts were washed with water (10 ml), saturated NaCl (10 ml)
  4. dry with materialdried over Na2SO4
  5. customthe solvent removed in vacuo
  6. customThe product was purified by silica gel chromatography
  7. washeluting with 10-20% EtOAc in hexanes

Sources & evidence

ORD record
ord-f53ddf3d5af44fe8be954af8ee7ad67d
Source dataset
uspto-grants-2015_11
Patent number
US09181271B2

Reaction notes

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