Dimethylformamide → 3-[2-Benzyl-6-(2-ethoxyethyl)oxy-3-pyridyl]ethynyl-3-quinuclidinol

HRID 1359383Notes

Reaction equation

HRID 1359383 reaction equation
CN(C)C=O.[CH2:6]([C:13]1[C:18](Br)=[CH:17][CH:16]=[C:15]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH3:25])[N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:26]([C:28]1([OH:36])[CH:33]2[CH2:34][CH2:35][N:30]([CH2:31][CH2:32]2)[CH2:29]1)#[CH:27].C(N(CC)CC)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C>[CH2:6]([C:13]1[C:18]([C:27]#[C:26][C:28]2([OH:36])[CH:33]3[CH2:34][CH2:35][N:30]([CH2:31][CH2:32]3)[CH2:29]2)=[CH:17][CH:16]=[C:15]([O:20][CH2:21][CH2:22][O:23][CH2:24][CH3:25])[N:14]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 181821972-Benzyl-3-bromo-6-(2-ethoxyethyl)oxypyridine

Product 1

HCID 181824373-[2-Benzyl-6-(2-ethoxyethyl)oxy-3-pyridyl]ethynyl-3-quinuclidinol

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

7 ml of N,N-dimethylformamide was added to a mixture of 2-benzyl-3-bromo-6-(2-ethoxyethyl)oxypyridine, 601 mg of 3-ethynyl-3-quinuclidinol, 406 mg of tetrakis(triphenylphosphine)palladium(0), 220 mg of cuprous iodide and 1.7 ml of triethylamine, followed by heating under stirring at 80° C. in an oil bath for one hour in a nitrogen atmosphere. After cooling as it was, ethyl acetate was added thereto. The mixture was filtered through Celite, and it was washed with aqueous ammonia. The organic phase was washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The residue was subjected to NH-silica gel column chromatography using ethyl acetate/hexane as an eluent for separation and purification, to give 247 mg of the target compound.

Workup

  1. temperatureby heating
  2. temperatureAfter cooling as it
  3. filtrationThe mixture was filtered through Celite, and it
  4. washwas washed with aqueous ammonia
  5. washThe organic phase was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was removed
  8. customfor separation and purification

Sources & evidence

ORD record
ord-90f22ee504584637a2a713c95a383ad4
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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