Cesium carbonate → (S)-4-((4-Chloro-3-methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl ester

HRID 449838ノート

反応式

HRID 449838 の反応式
[C:1]([C:3]1[CH:11]=[CH:10][C:9]2[NH:8][C:7]3[CH2:12][C@@H:13]([NH:15][C:16](=[O:21])[O:17][CH:18]([CH3:20])[CH3:19])[CH2:14][C:6]=3[C:5]=2[CH:4]=1)#[N:2].[Cl:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([CH2:29]Cl)[C:24]=1[O:31][CH3:32].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.O>[CH:18]([O:17][C:16](=[O:21])[NH:15][C@@H:13]1[CH2:12][C:7]2[N:8]([CH2:29][C:25]3[C:24]([O:31][CH3:32])=[C:23]([Cl:22])[CH:28]=[CH:27][N:26]=3)[C:9]3[CH:10]=[CH:11][C:3]([C:1]#[N:2])=[CH:4][C:5]=3[C:6]=2[CH2:14]1)([CH3:19])[CH3:20]

参加物

6

反応物 3

HCID 10796Cesium carbonateHCID 118163554-chloro-2-(chloromethyl)-3-methoxypyridineHCID 66933207(S)-(7-Cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)carbamic Acid Isopropyl Ester

生成物 1

HCID 66933264(S)-4-((4-Chloro-3-methoxypyridin-2-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl ester収率 92.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of (S)-isopropyl 7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamate (680 mg, 2.40 mmol) and 4-chloro-2-(chloromethyl)-3-methoxypyridine (553 mg, 2.88 mmol) in dimethylformamide (5 mL) is added cesium carbonate (1.17 g, 3.60 mmol) and the mixture stirred at room temperature overnight. The reaction mixture is diluted with water and the beige solid is filtered. It is rinsed with water and then dried in a vacuum oven at 50° C. for 48 h to obtain a gray solid (970 mg, 92%). LC-ES/MS m/z 439.0 [M+H]+.

後処理

  1. filtrationthe beige solid is filtered
  2. washIt is rinsed with water
  3. customdried in a vacuum oven at 50° C. for 48 h

出典と根拠

ORDレコード
ord-b2b72a8912e445fea1fc50c7d716149b
出典データセット
uspto-grants-2013_07
特許番号
US08486943B2

反応ノート

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