Pyrrolidine → 5-Bromo-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine

HRID 271638

Reaktionsgleichung

Reaktionsgleichung von HRID 271638
CS(Cl)(=O)=O.[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[C:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23]O)=[CH:19][CH:18]=2)=[N:11][CH:12]=1.C([N:27]([CH:31]([CH3:33])C)[CH:28]([CH3:30])C)C.N1CCCC1>C(Cl)Cl>[Br:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]#[C:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][N:27]3[CH2:28][CH2:30][CH2:33][CH2:31]3)=[CH:19][CH:18]=2)=[N:11][CH:12]=1

Komponenten

6

Edukt 4

HCID 31268Pyrrolidine2×HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69070552{4-[4-(5-Bromo-pyridin-2-yl)-but-3-ynyl]-phenyl}-methanol

Produkt 1

HCID 690713915-Bromo-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

0.24 mL (3.04 mmol) methanesulphonic acid chloride are added to a solution, cooled to 0° C., of 800 mg (2.53 mmol) {4-[4-(5-bromo-pyridin-2-yl)-but-3-ynyl]-phenyl}-methanol in 17 mL DCM and then a solution of 0.52 mL ethyldiisopropylamine in 3 mL DCM is added dropwise. The mixture is stirred for a further 30 min at 0° C., 0.51 mL (6.08 mmol) pyrrolidine is added, the reaction mixture is heated to RT and kept at this temperature for 5 h. To complete the reaction another 0.26 mL (3 mmol) pyrrolidine are added and stirred for 1 h at RT. The mixture is evaporated down i.vac., combined with 10 mL water and 20 ml EtOAc, acidified with 1 M HCl and the organic phase is separated off. The aqueous phase is made alkaline with 2 M Na2CO3 solution, extracted with 20 mL EtOAc, the organic phase is separated off and dried over Na2SO4. After the desiccant and solvent have been eliminated the desired product is obtained.

Aufarbeitung

  1. temperaturethe reaction mixture is heated to RT
  2. waitkept at this temperature for 5 h
  3. additionare added
  4. stirringstirred for 1 h at RT
  5. customThe mixture is evaporated down i.vac
  6. customthe organic phase is separated off
  7. extractionextracted with 20 mL EtOAc
  8. customthe organic phase is separated off
  9. dry with materialdried over Na2SO4
  10. customis obtained

Quellen und Nachweise

ORD-Eintrag
ord-9d62424f6eba4cb48ad416fb957acb80
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07452911B2

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