Triethylamine → 3-Chloro-6-((trimethylsilyl)ethynyl)isoquinoline

HRID 523064Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

A suspension of 6-bromo-3-chloroisoquinoline (240 mg, 1 mmol), ethynyltrimethylsilane (150 mg, 1.5 mmol), triethylamine (150 mg, 1.5 mmol), copper iodide (20 mg, 0.1 mmol), triphenylphosphine (26 mg, 0.1 mmol), and palladium acetate (22.4 mg, 1 mmol) in dry DMF (1 mL) was heated at 65° C. for 30 minutes. The reaction was cooled to room temperature and diluted with ethyl acetate (20 mL). The organic solution was washed with water (20 mL), brine (20 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to afford the title compound as a white powder (180 mg, 70%).

Workup

temperatureThe reaction was cooled to room temperature
washThe organic solution was washed with water (20 mL), brine (20 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by silica gel column chromatography
washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record: ord-d77cea21d8aa47c39f66673543160956
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334286B2

Reaction notes

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