1,2-Dichloroethane → HCID 66605774, compound

HRID 2410816Notes

Reaction equation

HRID 2410816 reaction equation
ClCCCl.[N:5]([C:8]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)=[N:16][C:15]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[N+]=[N-]>C(Cl)Cl.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.[Rh].[Rh]>[N+:24]([C:21]1[CH:20]=[CH:19][C:18]2[C:17]3[N:16]=[C:15]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:35])([F:36])[F:34])[CH:28]=4)[CH:14]=[C:9]([C:10]([O:12][CH3:13])=[O:11])[C:8]=3[NH:5][C:23]=2[CH:22]=1)([O-:26])=[O:25]

Participants

5

Reactant 2

HCID 111,2-DichloroethaneHCID 86663053HCID 86663053, compound

Product 1

HCID 66605774HCID 66605774, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 6099591Rhodium(II) Octanoate DimerCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
80 °C

Procedure

1,2-Dichloroethane (10 mL) was added to a mixture of methyl 3-azido-2-(4-nitrophenyl)-6-(3-(trifluoromethyl)phenyl)isonicotinate (1.0 g, 2.3 mmol), rhodium octanoate dimer (0.125 g, 0.161 mmol) and crushed 4A° molecular sieves (1.0 g). The reaction was heated at 80° C. for 20 hr. The crude mixture was diluted with DCM and silica gel chromatography (step gradient elution with DCM containing 0 to 20% MeOH) afforded methyl 7-nitro-2-(3-(trifluoromethyl)phenyl)-5H-pyrido[3,2-b]indole-4-carboxylate (400 mg, 0.963 mmol, 43% yield). MS (ESI) m/z 416.09 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 12.24 (1H, br s), 8.42-8.72 (5H, m), 8.16 (1H, dd, J=8.55, 1.83 Hz), 7.82 (2H, ddd, J=15.11, 7.78, 7.63 Hz), 4.10 (3H, s).

Workup

  1. customcrushed 4A° molecular sieves (1.0 g)

Sources & evidence

ORD record
ord-ba2058b42210405f9a4a8e1bdc602e5d
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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