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

HRID 449837ノート

反応式

HRID 449837 の反応式
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8]Cl.[CH:10]([O:13][C:14](=[O:30])[NH:15][C@@H:16]1[CH2:29][C:19]2[NH:20][C:21]3[CH:22]=[CH:23][C:24]([C:27]#[N:28])=[CH:25][C:26]=3[C:18]=2[CH2:17]1)([CH3:12])[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C.ClCCl.O>[CH:10]([O:13][C:14](=[O:30])[NH:15][C@@H:16]1[CH2:29][C:19]2[N:20]([CH2:8][C:7]3[CH:6]=[CH:5][N:4]=[CH:3][C:2]=3[Br:1])[C:21]3[CH:22]=[CH:23][C:24]([C:27]#[N:28])=[CH:25][C:26]=3[C:18]=2[CH2:17]1)([CH3:12])[CH3:11]

参加物

8

反応物 3

HCID 10796Cesium carbonateHCID 66933207(S)-(7-Cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)carbamic Acid Isopropyl EsterHCID 669333093-Bromo-4-(chloromethyl)pyridine

生成物 1

HCID 66933638(S)-4-((3-Bromopyridin-4-yl)methyl)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-ylcarbamic acid isopropyl ester収率 118.8%

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 3-bromo-4-(chloromethyl)pyridine (3.16 g, 11.5 mmol), ((S)-7-cyano-1,2,3,4-tetrahydro-cyclopenta[b]indol-2-yl)-carbamic acid isopropyl ester (2.50 g, 8.82 mmol) and cesium carbonate (4.31 g, 13.2 mmol) in dimethylformamide (20 mL) is stirred at room temperature under nitrogen overnight. The reaction mixture is then diluted with ethyl acetate, dichloromethane, and water. The organic phase is separated, washed with water twice, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo to obtain a brown oil (˜4.75 g). The oil is triturated with hexanes twice, then with ether twice. It is then purified by flash chromatography eluting with 30 to 60% ethyl acetate/hexanes to obtain an off-white solid (3.23 g, 81%). LC-ES/MS m/z (79Br/81Br) 453.0/455.0 [M+H]+.

後処理

  1. customThe organic phase is separated
  2. washwashed with water twice
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-912c5da85ab34d98bd5e00be39c125d9
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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