Triethylamine → HCID 58574504, compound

HRID 1619359Notes

Reaction equation

HRID 1619359 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[N:7]3[CH2:20][CH2:19][C:14]4([O:18][CH2:17][CH2:16][O:15]4)[CH2:13][CH2:12][C:8]3=[N:9]2)=[CH:4][CH:3]=1.[C:22]([Si:24]([CH3:27])([CH3:26])[CH3:25])#[CH:23].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC>CN(C=O)C.O.CC([O-])=O.CC([O-])=O.[Pd+2].[Cu]I>[CH3:25][Si:24]([C:22]#[C:23][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:21])[N:7]3[CH2:20][CH2:19][C:14]4([O:18][CH2:17][CH2:16][O:15]4)[CH2:13][CH2:12][C:8]3=[N:9]2)=[CH:4][CH:3]=1)([CH3:27])[CH3:26]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 58574404HCID 58574404, compound

Product 1

HCID 58574504HCID 58574504, compound

Reagents, catalysts & solvents 4

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

Procedure

A solution of 3-bromo-9,10-dihydro-6H-spiro[azepino[2,1-b]quinazoline-8,2′-[1,3]dioxolan]-12(7H)-one (1.74 g, 4.96 mmol, 1 equiv), ethynyltrimethylsilane (972 mg, 9.92 mmol, 2 equiv), Pd(OAc)2 (223.2 mg, 0.992 mmol, 0.2 equiv), PPh3 (1.04 g, 3.96 mmol, 0.8 equiv), CuI (189 mg, 0.992 mmol, 0.2 equiv) and Et3N (1.3 mL) in DMF (50 mL) was stirred in a sealed tube 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 (3×100 mL). The combined organic layers were washed with brine and dried over anhydrous sodium sulfate, then concentrated under reduced pressure. The product was obtained by silica gel chromatography purification.

Workup

  1. extractionextracted with ethyl acetate (3×100 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe product was obtained by silica gel chromatography purification

Sources & evidence

ORD record
ord-2887b101e30649c3b5491c507b1e02cd
Source dataset
uspto-grants-2014_07
Patent number
US08772301B2

Reaction notes

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