Triethylamine → HCID 19592364, compound

HRID 613471Notes

Reaction equation

HRID 613471 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[N+:12]([O-:14])=[O:13].[CH3:15][Si:16]([C:19]#[CH:20])([CH3:18])[CH3:17].C(N(CC)CC)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(#N)C.C(OCC)C.[Pd](Cl)Cl.[Cu]I>[N+:12]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[N:4]=[CH:3][C:2]([C:20]#[C:19][Si:16]([CH3:18])([CH3:17])[CH3:15])=[CH:11]2)([O-:14])=[O:13]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 66111TrimethylsilylacetyleneHCID 79286Quinoline, 3-bromo-8-nitro-

Product 1

HCID 19592364HCID 19592364, compoundYield 65.5%

Reagents, catalysts & solvents 4

HCID 24290Palladium ChlorideCatalystHCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-bromo-8-nitroquinoline (300 mg), trimethylsilylacetylene (140 mg), palladium (II) chloride (38 mg), catalytic amount of copper (I) iodide, triethylamine (3 ml) and triphenylphosphine (113 mg) in acetonitrile (3 ml) was stirred for 3 hours at ambient temperature. The mixture was diluted with diethyl ether, and insoluble material was filtered off. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography on silica gel (n-hexane-ethyl acetate) to give 8-nitro-3-(trimethylsilylethynyl)quinoline (210 mg).

Workup

  1. filtrationwas filtered off
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica gel (n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-55bcaa7bf66a4f86b38b541b162c6064
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

Loading…