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Sodium Bicarbonate → (2R)-N-{[5-bromo-1-(3-methoxypropyl)indol-3-yl]methyl}-N-cyclopropylmorpholin-2-carboxamide

HRID 872006
ノート
印刷プレビュー

反応式

HRID 872006 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[C:5]2[CH2:16][N:17]([CH:33]1[CH2:35][CH2:34]1)[C:18]([C@@H:20]1[O:25][CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]1)=[O:19].C(=O)(O)[O-].[Na+]>ClCCCl.[Br-].[Zn+2].[Br-]>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][CH2:13][O:14][CH3:15])[CH:6]=[C:5]2[CH2:16][N:17]([CH:33]1[CH2:35][CH2:34]1)[C:18]([C@@H:20]1[O:25][CH2:24][CH2:23][NH:22][CH2:21]1)=[O:19]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 59494589HCID 59494589、化合物

生成物 1

HCID 59494802(2R)-N-{[5-bromo-1-(3-methoxypropyl)indol-3-yl]methyl}-N-cyclopropylmorpholin-2-carboxamide

試薬・触媒・溶媒 2

HCID 10421208Zinc bromide触媒HCID 111,2-Dichloroethane溶媒

反応条件

温度
40 °C

実験手順

Zinc bromide (209 mg) was added to a solution of tert-butyl(2R)-2-{[{[5-bromo-1-(3-methoxypropyl)indol-3-yl]methyl}(cyclopropyl)amino]carbonyl}morpholin-4-carboxylate (a compound of Reference Example 128, 200 mg) in 1,2-dichloroethane (12 ml) and the mixture was stirred at 40° C. for 3 hours. The reaction mixture was poured into a saturated aqueous solution of sodium bicarbonate and extracted with chloroform. The organic layer was washed with water and saturated brine, dried over magnesium sulfate and concentrated in vacuo. The resulted residue was purified with a silica gel column chromatography (eluting solvent: chloroform/methanol=98/2 to 93/7) to give (2R)—N-{[5-bromo-1-(3-methoxypropyl)indol-3-yl]methyl}-N-cyclopropylmorpholin-2-carboxamide (117 mg) as a colorless oil.

後処理

  1. extractionextracted with chloroform
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulted residue was purified with a silica gel column chromatography (eluting solvent: chloroform/methanol=98/2 to 93/7)

出典と根拠

ORDレコード
ord-2da09ada2c9140af8df81b64e5c246cb
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08975252B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート