Triethylamine → HCID 58574262, compound

HRID 1619331Notes

Reaction equation

HRID 1619331 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:16])[N:7]3[CH2:15][CH2:14][NH:13][CH2:12][C:8]3=[N:9]2)=[CH:4][CH:3]=1.[C:17]([Si:19]([CH3:22])([CH3:21])[CH3:20])#[CH:18].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC>O.CC([O-])=O.CC([O-])=O.[Pd+2].[Cu]I.CN(C=O)C>[CH3:20][Si:19]([C:17]#[C:18][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:16])[N:7]3[CH2:15][CH2:14][NH:13][CH2:12][C:8]3=[N:9]2)=[CH:4][CH:3]=1)([CH3:22])[CH3:21]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 58574180HCID 58574180, compound

Product 1

HCID 58574262HCID 58574262, compoundYield 56.8%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A flask was charged with 9-bromo-3,4-dihydro-1H-pyrazino[2,1-b]quinazolin-6(2H)-one (200 mg, 0.71 mmol, 1 equiv), ethynyltrimethylsilane (206 mg, 2.1 mmol, 3 equiv), Pd(OAc)2 (31.5 mg, 0.14 mmol, 0.2 equiv), PPh3 (165 mg, 0.63 mmol, 0.9 equiv), CuI (13 mg, 0.07 mmol, 0.1 equiv), Et3N (353 mg, 3.5 mmol, 5 equiv) and DMF (20 mL). A vacuum was applied and the reaction mixture was back filled with nitrogen three times. The mixture was stirred at 70° C. for 3.5 hours. After it was cooled to room temperature, the reaction mixture was diluted with H2O and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate, then concentrated under reduced pressure. 120 mg of desired product was obtained MS (ESI): 298 (MH+).

Workup

  1. additionthe reaction mixture was back filled with nitrogen three times
  2. temperatureAfter it was cooled to room temperature
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-724c396c509a4301b1b234e77155366e
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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