Methane → 2-[6-[(6-Bromohexyl)oxy]-1-hexynyl]-4-pyridinecarboxamide

HRID 1649791Notes

Reaction equation

HRID 1649791 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([NH2:10])=[O:9])[CH:5]=[CH:4][N:3]=1.[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[CH:24].C1(NC2CCCCC2)CCCCC1.C>C(#N)C.CCOCC.C(O)C.C1(C)C=CC=CC=1.[Cu]I>[Br:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]#[C:24][C:2]1[CH:7]=[C:6]([C:8]([NH2:10])=[O:9])[CH:5]=[CH:4][N:3]=1

Participants

9

Reactant 4

HCID 297MethaneHCID 7582DicyclohexylamineHCID 46254072-BromoisonicotinamideHCID 218671586-[(6-Bromohexyl)oxy]-1-hexyne

Product 1

HCID 198547972-[6-[(6-Bromohexyl)oxy]-1-hexynyl]-4-pyridinecarboxamide

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolventHCID 21863594Toluene ethanolSolvent

Procedure

A mixture of 2-bromo-4-pyridinecarboxamide (1.1 g), BTPC (35 mg), copper (I) iodide (8 mg), 6-[(6-bromohexyl)oxy]-1-hexyne (1.43 g) and dicyclohexylamine (1.2 ml) in acetonitrile (20 ml) was stirred at room temperature, under nitrogen, for 20 h, then left to stand for 24 h. The yellow mixture was diluted with ether (50 ml), filtered, the filtrate dried and evaporated in vacuo to give a yellow waxy solid. The solid was purified by FCC eluting with System A (98:2:1) to give a pale yellow waxy solid. The solid was dissolved in ethanol:toluene (1:1), (20 ml) treated with activated charcoal (0.2 g), heated, filtered through hyflo and evaporated in vacuo to give the title compound as a pale yellow waxy solid (1.04 g), t.l.c. (toluene-ethanol: 0.880 ammonia, 90:10:1) Rf 0.31.

Workup

  1. waitleft
  2. waitto stand for 24 h
  3. filtrationfiltered
  4. customthe filtrate dried
  5. customevaporated in vacuo
  6. customto give a yellow waxy solid
  7. customThe solid was purified by FCC
  8. washeluting with System A (98:2:1)
  9. customto give a pale yellow waxy solid
  10. temperatureheated
  11. filtrationfiltered through hyflo
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-f82c52a647f04a55a9d54a0117cf832c
Source dataset
uspto-grants-1990_05
Patent number
US04921867

Reaction notes

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