2-Chloropyridine → HCID 67382629, compound

HRID 2176919Notes

Reaction equation

HRID 2176919 reaction equation
[CH:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C:3](=[O:9])[NH:2]2.Cl[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=1.C([O-])([O-])=O.[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.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>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[N:2]1[C:3](=[O:9])[CH:4]2[CH2:7][CH2:8][CH:1]1[CH2:6][CH2:5]2

Participants

7

Reactant 4

HCID 79772-ChloropyridineHCID 10796Cesium carbonateHCID 1378872-Azabicyclo(2.2.2)octan-3-oneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)

Product 1

HCID 67382629HCID 67382629, compoundYield 61.9%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 2-azabicyclo[2.2.2]octan-3-one (0.6 g, 4.8 mmol), 2-chloropyridine (0.65 g, 5.76 mmol), Cs2CO3 (2.36 g, 7.20 mmol) and xantphos (0.22 g, 0.38 mmol) in 1,4-dioxane (30 ml) was purged with argon gas for 15 min. Tetrakis(triphenylphosphine)palladium (0) (0.22 g, 0.19 mmol) was added and continued purging for another 10 min. The reaction mixture was heated at 125° C. for 3 h. The reaction mixture was cooled to room temperature and filtered. The filtrate was concentrated and dried under reduced pressure to afford the crude compound. Purification by column chromatography over neutral alumina using 15% ethyl acetate in petroleum ether as eluent afforded 600 mg (61.9%) of 2-(pyridin-2-yl)-2-aza-bicyclo[2.2.2]octan-3-one as pale yellow solid.

Workup

  1. customwas purged with argon gas for 15 min
  2. customcontinued purging for another 10 min
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customdried under reduced pressure
  7. customto afford the crude compound
  8. customPurification by column chromatography over neutral alumina using 15% ethyl acetate in petroleum ether as eluent

Sources & evidence

ORD record
ord-5feb142a9b7b4ecb9f21859d53e7bfc5
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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