Triethylamine → 3-[4-Benzyl-2-(3-hydroxy-1-butynyl)-5-pyridyl]ethynyl-3-quinuclidinol

HRID 1359391Notes

Reaction equation

HRID 1359391 reaction equation
[CH2:1]([C:8]1[C:13](Br)=[CH:12][N:11]=[C:10]([C:15]#[C:16][CH:17]([OH:19])[CH3:18])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([C:22]1([OH:30])[CH:27]2[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]2)[CH2:23]1)#[CH:21].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.CN1CCCC1=O>[CH2:1]([C:8]1[C:13]([C:21]#[C:20][C:22]2([OH:30])[CH:27]3[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]3)[CH2:23]2)=[CH:12][N:11]=[C:10]([C:15]#[C:16][CH:17]([OH:19])[CH3:18])[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 36135173-Ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 181823824-Benzyl-5-bromo-2-(3-hydroxy-1-butynyl)pyridine

Product 1

HCID 181824823-[4-Benzyl-2-(3-hydroxy-1-butynyl)-5-pyridyl]ethynyl-3-quinuclidinol

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

110 mg of 4-benzyl-5-bromo-2-(3-hydroxy-1-butynyl)pyridine, 53 mg of 3-ethynyl-3-quinuclidinol, 50 mg of tetrakis(triphenylphosphine)palladium(0), 7 mg of cuprous iodide and 0.5 ml of triethylamine were added to 2 ml of 1-methyl-2-pyrrolidinone, followed by stirring for one hour in an oil bath kept at 100° C. After cooling as it was, it was evaporated. The residue was subjected to NH-silica gel column chromatography and eluted with 5% methanol/ethyl acetate, to synthesize 32 mg of the target compound.

Workup

  1. customkept at 100° C
  2. temperatureAfter cooling as it
  3. customit was evaporated
  4. washeluted with 5% methanol/ethyl acetate
  5. customto synthesize 32 mg of the target compound

Sources & evidence

ORD record
ord-823ee74cba334314866ede24e9b42dec
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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