Triethylamine → HCID 59699946, compound

HRID 729814Notes

Reaction equation

HRID 729814 reaction equation
[Br:1][C:2]1[CH:3]=[C:4](I)[C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1.C(N(CC)CC)C.[CH3:20][Si:21]([C:24]#[CH:25])([CH3:23])[CH3:22]>ClCCl.Cl[Pd-2](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.[Cu]I>[Br:1][C:2]1[CH:3]=[C:4]([C:25]#[C:24][Si:21]([CH3:23])([CH3:22])[CH3:20])[C:5]([NH:8][C:9](=[O:11])[CH3:10])=[N:6][CH:7]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 59699934HCID 59699934, compound

Product 1

HCID 59699946HCID 59699946, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418903HCID 178418903, compoundCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of N-(5-bromo-3-iodo-pyridin-2-yl)-acetamide (6.42 g, 18.83 mmol) in dichloromethane (90 ml) was added triethyl amine (3.15 ml, 22.6 mmol), then the mixture was cooled to 0° C. and dichlorobis(triphenylphosphino)palladium (II) (66 mg, 0.094 mmol) and copper(i) iodide (36 mg, 0.188 mmol) were added sequentially. Finally trimethylsilylacetylene (2.93 ml, 20.71 mmol) was added dropwise, and the ice bath was removed. After stirring at room temperature for 17 hours, the crude mixture was directly adsorbed on silica gel. Purification by flash chromatography on silica gel with a gradient of ethyl acetate/hexane afforded the title compound as light yellow solid (4.75 g, 81% yield). 1H NMR (DMSO-d6): δ 9.99 (s, 1H), 8.31 (d, J=2.5 Hz, 1H), 7.95 (d, J=2.5 Hz, 1H), 1.82 (s, 3H), 0.00 (s, 9H); HPLC/MS m/z: 311, 313 [MH]+.

Workup

  1. customthe ice bath was removed
  2. customPurification by flash chromatography on silica gel with a gradient of ethyl acetate/hexane

Sources & evidence

ORD record
ord-e9d9c312798e419087dd8c9834560c7c
Source dataset
uspto-grants-2009_09
Patent number
US07582637B2

Reaction notes

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