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Potassium Carbonate → 1,1-Dimethylethyl 4-(5-bromo-2-pyridinyl)-1,4-diazepane-1-carboxylate

HRID 1640423
ノート
印刷プレビュー

反応式

HRID 1640423 の反応式
[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:16]1[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][N:17]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([N:4]2[CH2:5][CH2:6][CH2:7][N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH2:3]2)=[N:17][CH:18]=1
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

6

反応物 3

HCID 11430Potassium CarbonateHCID 693532,5-DibromopyridineHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

生成物 1

HCID 602095661,1-Dimethylethyl 4-(5-bromo-2-pyridinyl)-1,4-diazepane-1-carboxylate収率 91.5%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒
HCID 8857
Ethyl Acetate
溶媒

反応条件

温度
150 °C

実験手順

1.03 g (5 mmol) of 1,1-dimethylethyl 1,4-diazepane-1-carboxylate, 1.19 g (5 mmol) of 2,5-dibromopyridine and 0.7 g (5 mmol) of potassium carbonate suspended in 0.90 ml of dimethyl sulfoxide (DMSO) are introduced into an autoclave. The mixture is heated at 150° C. for 22 hours. The reaction mixture is allowed to cool to room temperature, it is taken up in ethyl acetate, and the organic solution is washed with water and then brine, and dried over sodium sulfate. The filtrate is concentrated under reduced pressure and the residue thus obtained is purified by chromatography on silica gel, eluting with a 99.5/0.5 mixture of dichloromethane and methanol. 1.63 g of product are obtained in the form of an oil, and are used without further purification in the following step.

後処理

  1. additionare introduced into an autoclave
  2. temperatureto cool to room temperature
  3. washthe organic solution is washed with water
  4. dry with materialbrine, and dried over sodium sulfate
  5. concentrationThe filtrate is concentrated under reduced pressure
  6. customthe residue thus obtained
  7. customis purified by chromatography on silica gel
  8. washeluting with a 99.5/0.5 mixture of dichloromethane and methanol

出典と根拠

ORDレコード
ord-e650480134f94486a6779671c8dd79b3
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08114866B2

反応ノート

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