Cesium carbonate → dimethyl 13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate

HRID 1982924Notes

Reaction equation

HRID 1982924 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]3C(O)[C:21]4[C:26]([C:8]=23)=[CH:25][CH:24]=[C:23]([O:27][CH3:28])[CH:22]=4)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.COP([C:36](=[CH2:41])[C:37]([O:39][CH3:40])=[O:38])(OC)=O.[C:42](=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.O>[CH:1]1([C:7]2[C:15]3[CH:14]=[CH:13][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:11][C:10]=3[N:9]3[CH2:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:42][C:21]4[CH:22]=[C:23]([O:27][CH3:28])[CH:24]=[CH:25][C:26]=4[C:8]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 3016938Methyl 2-(dimethoxyphosphinyl)acrylateHCID 59682118methyl 11-cyclohexyl-6-hydroxy-8-methoxy-6H-isoindolo[2,1-a]indole-3-carboxylate

Product 1

HCID 58765200dimethyl 13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylateYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 11-cyclohexyl-6-hydroxy-8-methoxy-6H-isoindolo[2,1-a]indole-3-carboxylate (2.9 g, 7.4 mmol), methyl 2-(dimethoxyphosphoryl)acrylate (2.6 g, 11 mmol), cesium carbonate (3.6 g, 11 mmol) in DMF (20 mL) was heated at 60° C. for 2 h and cooled to rt. The stirring reaction mixture was diluted with H2O (50 mL) and the precipitates were collected by filtration to yield dimethyl 13-cyclohexyl-3-methoxy-7H-indolo[2,1-a][2]benzazepine-6,10-dicarboxylate (3.3 g, 7.1 mmol, 97%) as a yellow solid which was used without further purification. LCMS: m/e 460 (M+H)+, ret time 3.35 min, column B, 3 minute gradient.

Workup

  1. customThe stirring reaction mixture
  2. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-b3e958e158514fb5a374715f81b83c2c
Source dataset
uspto-grants-2009_06
Patent number
US07541351B2

Reaction notes

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