Morpholine → 4-{4-[4-(5-Bromo-pyridin-2-yl)-but-3-ynyl]-benzyl}-morpholine

HRID 271640

反応式

HRID 271640 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(C(C)C)C(C)C)C.[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>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:18]=[CH:19][C:20]([CH2:23][N:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[CH:21][CH:22]=2)=[N:11][CH:12]=1

参加物

6

反応物 4

HCID 8083MorpholineHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69070552{4-[4-(5-Bromo-pyridin-2-yl)-but-3-ynyl]-phenyl}-methanol

生成物 1

HCID 690796844-{4-[4-(5-Bromo-pyridin-2-yl)-but-3-ynyl]-benzyl}-morpholine

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

36 μL (0.46 mmol) methanesulphonic acid chloride are added to a solution, cooled to 0° C., of 120 mg (0.38 mmol) {4-[4-(5-bromo-pyridin-2-yl)-but-3-ynyl]-phenyl}-methanol (Example 2.20a) in 5 mL DCM. A solution of 78 μL (0.46 mmol) ethyldiisopropylamine in 1 mL DCM is slowly added dropwise, the mixture is stirred for a further 30 min at 0° C., then 80 μL (0.92 mmol) of morpholine are added, the mixture is allowed to come up to RT and kept at RT for 2 h. The mixture is evaporated down i.vac., the residue is combined with 20 mL EtOAc and 10 mL water, acidified with 1 M HCl and the phases are separated. The aqueous phase is combined with 2 M Na2CO3 solution, extracted with 20 mL EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the product is obtained.

後処理

  1. customto come up to RT
  2. waitkept at RT for 2 h
  3. customThe mixture is evaporated down i.vac
  4. customthe phases are separated
  5. extractionextracted with 20 mL EtOAc
  6. dry with materialthe organic phase is dried over Na2SO4
  7. customis obtained

出典と根拠

ORDレコード
ord-c8f8424bdfa542bcad375fc370055782
出典データセット
uspto-grants-2008_11
特許番号
US07452911B2

関連ノート

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