Pyrrolidine → 6-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-4-methyl-2-pyrrolidin-1-ylquinoline

HRID 2112817Notes

Reaction equation

HRID 2112817 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl[C:7]1[CH:16]=[C:15]([CH3:17])[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:18]#[C:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)=[CH:22][N:21]=3)[CH:13]=2)[N:8]=1>O1CCOCC1>[Cl:32][C:29]1[CH:28]=[CH:27][C:26]([C:23]2[CH:24]=[CH:25][C:20]([C:19]#[C:18][C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][CH:11]=3)[N:8]=[C:7]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:16]=[C:15]4[CH3:17])=[N:21][CH:22]=2)=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 860798502-Chloro-6-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-4-methylquinoline

Product 1

HCID 576432376-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-4-methyl-2-pyrrolidin-1-ylquinoline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

77 μL (0.925 mmol) of pyrrolidine is added to a solution of 90 mg (0.231 mmol) of 2-chloro-6-[5-(4-chlorophenyl)pyridin-2-ylethynyl]-4-methylquinoline in 5 mL of 1,4-dioxane and the reaction mixture is refluxed overnight. It is evaporated down in vacuo, and the residue is taken up in DMF and purified by HPLC-MS. The fractions containing the product are combined, evaporated down, and freeze-dried. The product is dissolved in DCM, evaporated down, and the residue is triturated with a little EtOAc, filtered, washed again with a little EtOAc, and dried at 50° C. in the circulating air dryer. Yield: 39 mg (39% of theoretical); C27H22ClN3 (M=423.936); calc.: molpeak (M+H)+: 424/426 (Cl); found: molpeak (M+H)+: 424/426 (Cl); HPLC-MS: 5.8 min (method A).

Workup

  1. temperaturethe reaction mixture is refluxed overnight
  2. customIt is evaporated down in vacuo
  3. custompurified by HPLC-MS
  4. additionThe fractions containing the product
  5. customevaporated down
  6. customfreeze-dried
  7. dissolutionThe product is dissolved in DCM
  8. customevaporated down
  9. customthe residue is triturated with a little EtOAc
  10. filtrationfiltered
  11. washwashed again with a little EtOAc
  12. customdried at 50° C. in the circulating air dryer
  13. custom5.8 min (method A)

Sources & evidence

ORD record
ord-2c31e77f74af4bc0bc40fc81d69605ef
Source dataset
uspto-grants-2009_04
Patent number
US07524862B2

Reaction notes

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