2,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine → HCID 90338558, compound

HRID 1508961Notes

Reaction equation

HRID 1508961 reaction equation
Cl[C:2]1[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][C:5]2=[C:4]([Cl:11])[CH:3]=1.C([Sn](CCCC)(CCCC)[C:17]1[O:18][CH:19]=[CH:20][N:21]=1)CCC>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>[Cl:11][C:4]1[CH:3]=[C:2]([C:17]2[O:18][CH:19]=[CH:20][N:21]=2)[N:7]=[C:6]2[CH2:8][CH2:9][CH2:10][C:5]=12

Participants

5

Reactant 2

HCID 122148172,4-Dichloro-6,7-dihydro-5H-cyclopenta[b]pyridineHCID 154861832-(Tri-n-butylstannyl)oxazole

Product 1

HCID 90338558HCID 90338558, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 2,4-dichloro-6,7-dihydro-5H-cyclopenta[b]pyridine (0.152 g, 0.81 mmol) in dioxane (3 mL) was added 2-(tributylstannyl)oxazole (0.318 g, 0.89 mmol) and tetrakis(triphenylphosphine)palladium (0.046 g, 0.040 mmol). The mixture was purged with nitrogen and then heated to 110° C. under sealed conditions for 16 h. After this time, the mixture was diluted with water and extracted with ethyl acetate. The organic layer were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, hexanes/ethyl acetate) to afford the title compound (0.061 g, 34%) as a white solid. MW=220.66. 1H NMR (CDCl3, 500 MHz) δ 7.94 (s, 1H), 7.78 (s, 1H), 7.29 (s, 1H), 3.19 (t, J=7.5 Hz, 2H), 3.06 (t, J=7.5 Hz, 2H), 2.22 (quin, J=7.5 Hz, 2H); APCI MS m/z 221 [M+H]+.

Workup

  1. customThe mixture was purged with nitrogen
  2. additionAfter this time, the mixture was diluted with water
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by column chromatography (silica, hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-6dac63e83635445498518a0c5ab6633c
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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