Dimethylformamide → HCID 18182334, compound

HRID 1359335Notes

Reaction equation

HRID 1359335 reaction equation
CN(C)C=O.FC(F)(F)S(O[C:12]1[C:13]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:14][C:15]([CH2:18][CH2:19][C:20](=[O:24])[CH2:21][O:22][CH3:23])=[CH:16][CH:17]=1)(=O)=O.[C:34]([C:36]1([OH:44])[CH:41]2[CH2:42][CH2:43][N:38]([CH2:39][CH2:40]2)[CH2:37]1)#[CH:35].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>[CH2:25]([C:13]1[C:12]([C:35]#[C:34][C:36]2([OH:44])[CH:41]3[CH2:42][CH2:43][N:38]([CH2:39][CH2:40]3)[CH2:37]2)=[CH:17][CH:16]=[C:15]([CH2:18][CH2:19][C:20](=[O:24])[CH2:21][O:22][CH3:23])[N:14]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 18182478HCID 18182478, compound

Product 1

HCID 18182334HCID 18182334, compoundYield 68.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

10 ml of N,N-dimethylformamide was added to a mixture of 1.9 g of 2-benzyl-6-(4-methoxy-3-oxobutyl)-3-pyridyl trifluoromethanesulfonate, 773 mg of 3-ethynyl-3-quinuclidinol, 525 mg of tetrakis(triphenylphosphine)palladium(0), 267 mg of cuprous iodide and 2.2 ml of triethylamine, followed by stirring for one hour at 50° C. in an oil bath in a nitrogen atmosphere. After cooling as it was, ethyl acetate was added thereto. The mixture was filtered through Celite, followed by washing with water. The organic phase was washed with brine, dried over anhydrous sodium sulfate and the solvent was removed. The residue was subjected to silica gel column chromatography using chloroform/methanol/36% aqueous ammonia (46:5:0.5) as an eluent for separation and purification, to give 1.3 g of the target compound.

Workup

  1. temperatureAfter cooling as it
  2. filtrationThe mixture was filtered through Celite
  3. washby washing with water
  4. washThe organic phase was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed
  7. customfor separation and purification

Sources & evidence

ORD record
ord-a7b1fc8f28fb402fa06601dd894d98fd
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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