Triethylamine → HCID 21107197, compound

HRID 1869916Notes

Reaction equation

HRID 1869916 reaction equation
Br[C:2]1[CH:11]=[C:10]([O:12][CH3:13])[C:9]2[CH:8]([N:14]([CH:16]3[CH2:18][CH2:17]3)[CH3:15])[CH2:7][CH2:6][C:5]([CH3:20])([CH3:19])[C:4]=2[CH:3]=1.C(N(CC)CC)C.[CH3:28][Si:29]([C:32]#[CH:33])([CH3:31])[CH3:30]>CCCCCC.[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>[CH:16]1([N:14]([CH3:15])[CH:8]2[CH2:7][CH2:6][C:5]([CH3:20])([CH3:19])[C:4]3[C:3]([C:33]#[C:32][Si:29]([CH3:31])([CH3:30])[CH3:28])=[CH:2][CH:11]=[C:10]([O:12][CH3:13])[C:9]2=3)[CH2:18][CH2:17]1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 21107132HCID 21107132, compound2×

Product 1

HCID 21107197HCID 21107197, compoundYield 80%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8058HexaneSolvent2×

Procedure

Following General Procedure D and using 2-bromo-5-(cyclopropyl-methylamino)-8,8-dimethyl-4-methoxy-5,6,7,8-tetrahydro-naphthalene (Intermediate 79, 1.08 g, 3.2 mmol), triethyl amine (5 mL), copper(I)iodide (0.061 g, 0.32 mmol), trimethylsilyl acetylene (3 mL, 21.1 mmol) and dichlorobis(triphenylphosphine)palladium(II) (0.225 g, 0.32 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using hexane-10% ethyl acetate in hexane as the eluent, the title compound (0.87 g, 80%) was obtained.

Sources & evidence

ORD record
ord-f905bee5528d46cdbb162f0df17d8453
Source dataset
uspto-grants-2009_12
Patent number
US07638648B2

Reaction notes

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