Triethylamine → HCID 59077770, compound

HRID 1359386Notes

Reaction equation

HRID 1359386 reaction equation
FC(F)(F)S(O[C:7]1[C:8]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:9][C:10]([O:13][CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)=[CH:11][CH:12]=1)(=O)=O.[C:30]([C@:32]1([OH:40])[CH:37]2[CH2:38][CH2:39][N:34]([CH2:35][CH2:36]2)[CH2:33]1)#[CH:31].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.CN(C)C=O>[CH2:21]([C:8]1[C:7]([C:31]#[C:30][C@:32]2([OH:40])[CH:37]3[CH2:38][CH2:39][N:34]([CH2:35][CH2:36]3)[CH2:33]2)=[CH:12][CH:11]=[C:10]([O:13][CH2:14][CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[N:9]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 946095(3R)-3-ethynyl-1-azabicyclo[2.2.2]octan-3-olHCID 18182207HCID 18182207, compound

Product 1

HCID 59077770HCID 59077770, compoundYield 71.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 428 mg of 2-benzyl-6-[(tetrahydro-4H-pyran-2-yl)methyloxy]-3-pyridyl trifluoromethanesulfonate, 180 mg of (3R)-3-ethynyl-3-quinuclidinol, 57.3 mg of tetrakis(triphenylphosphine)palladium(0), 1.9 mg of cuprous iodide, 415 μl of triethylamine and 5 ml of N,N-dimethylformamide was stirred at 90° C. for 3 hours in a nitrogen atmosphere. NH-silica gel was added to the reaction solution, and the solvent was removed. The residue was subjected to NH-silica gel column chromatography using 3% methanol/ethyl acetate, to give 305 mg of the target compound.

Workup

  1. additionNH-silica gel was added to the reaction solution
  2. customthe solvent was removed

Sources & evidence

ORD record
ord-79391ce8d7b5488487416afc24bc5d66
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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