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

HRID 271638ノート

反応式

HRID 271638 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9d62424f6eba4cb48ad416fb957acb80
出典データセット
uspto-grants-2008_11
特許番号
US07452911B2

反応ノート

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