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Potassium Carbonate → (R)-3-[2-Oxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid ethyl ester

HRID 2175186
ノート
印刷プレビュー

反応式

HRID 2175186 の反応式
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([NH:13][C:14]1[C:19]([N+:20]([O-])=O)=[CH:18][CH:17]=[C:16](C)[N:15]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].C[C:26]1[C:27]([CH3:42])=[C:28](C)[C:29]([CH3:40])=[C:30]2[C:34]=1[N:33]([CH3:35])[C:32](C)=[C:31]2[CH2:37]NI.[C:43]([O-])([O-])=[O:44].[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([N:13]1[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:19]2[N:20]([CH2:37][C:31]2[C:30]3[C:34](=[CH:26][C:27]([CH3:42])=[CH:28][C:29]=3[CH3:40])[N:33]([CH3:35])[CH:32]=2)[C:43]1=[O:44])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]
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 3

HCID 11430Potassium CarbonateHCID 58497430(R)-3-(6-Methyl-3-nitro-pyridin-2-ylamino)-3-phenyl-propionic acid ethyl esterHCID 131730211trimethyl-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-amino iodide

生成物 1

HCID 58497410(R)-3-[2-Oxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid ethyl ester収率 81%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
100 °C

実験手順

To a solution of (R)-3-(2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-3-phenyl-propionic acid ethyl ester (refer to example 2) (80 mg, 0.26 mmol) in DMF (10 mL) were added trimethyl-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-amino iodide (138 mg, 0.39 mmol) and K2CO3 (71 mg, 0.51 mmol) at room temperature. The solution was heated at 100° C. for 4 hours. The solution was cooled and was extracted with water and EtOAc. The combined organic layer was dried with MgSO4 and filtered. The filtrate was concentrated and the residue was purified by silica gel flash column chromatography with 20% EtOAc in Hexane as the eluent to afford the title compound (100 mg, 81%) as white foam.

後処理

  1. temperatureThe solution was cooled
  2. extractionwas extracted with water and EtOAc
  3. dry with materialThe combined organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by silica gel flash column chromatography with 20% EtOAc in Hexane as the eluent

出典と根拠

ORDレコード
ord-3112dc9392224cd2b212d672e67debcc
出典データセット
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09062056B2

反応ノート

読み込み中…

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