1,2-Dichloroethane → methyl 2-bromo-8-chloro-7-methoxy-5H-pyrido[3,2-b]indole-4-carboxylate

HRID 2410730노트

반응식

HRID 2410730 반응식
ClCCCl.[N:5]([C:8]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([Cl:26])[CH:19]=2)=[N:16][C:15]([Br:27])=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[N+]=[N-]>ClCCl.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.[Rh].[Rh]>[Br:27][C:15]1[CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:8]2[NH:5][C:23]3[CH:22]=[C:21]([O:24][CH3:25])[C:20]([Cl:26])=[CH:19][C:18]=3[C:17]=2[N:16]=1

참가 물질

5

반응물 2

HCID 111,2-DichloroethaneHCID 86663014Methyl 3-azido-6-bromo-2-(3-chloro-4-methoxyphenyl)isonicotinate

생성물 1

HCID 86663015methyl 2-bromo-8-chloro-7-methoxy-5H-pyrido[3,2-b]indole-4-carboxylate수율 56%

시약·촉매·용매 2

HCID 6099591Rhodium(II) Octanoate Dimer촉매HCID 6344Dichloromethane용매

반응 조건

온도
60 °C

실험 절차

1,2-Dichloroethane (0.1 mL) was added to a mixture of methyl 3-azido-6-bromo-2-(3-chloro-4-methoxyphenyl)isonicotinate (56 mg, 0.14 mmol), rhodium octanoate dimer (11 mg, 0.014 mmol) and crushed 4 A° molecular sieves (56 mg) in a microwave vial. The vial was sealed and heated at 60° C. overnight. The reaction was diluted with dichloromethane, filtered, and the solvents removed from the filtrate. Radial silica gel chromatography (step gradient with hexane containing 50 to 100% methylene chloride) of the residue afforded methyl 2-bromo-8-chloro-7-methoxy-5H-pyrido[3,2-b]indole-4-carboxylate (29 mg). MS (ESI) m/z 370.9 (M+H). 1H NMR (CDCl3) δ ppm 9.51 (1H, br. s.), 8.31 (1H, s), 7.89 (1H, s), 6.99 (1H, s), 4.05 (3H, s), 4.01 (3H, s).

후처리

  1. customcrushed 4 A° molecular sieves (56 mg) in a microwave vial
  2. customThe vial was sealed
  3. filtrationfiltered
  4. customthe solvents removed from the filtrate

출처 및 근거

ORD 기록
ord-9511fdecc95c436789c393ddb5e68623
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08815840B2

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