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

HRID 449837노트

반응식

HRID 449837 반응식
[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]

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 4

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-912c5da85ab34d98bd5e00be39c125d9
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08486943B2

반응 노트

불러오는 중…