1,2-Dichloroethane → HCID 86663049, compound

HRID 2410807Notes

Reaction equation

HRID 2410807 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]([Br:27])=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[N+]=[N-]>C1COCC1.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:19]3[CH:20]=[C:21]([N+:24]([O-:26])=[O:25])[CH:22]=[CH:23][C:18]=3[C:17]=2[N:16]=1

Participants

5

Reactant 2

HCID 111,2-DichloroethaneHCID 86663048HCID 86663048, compound

Product 1

HCID 86663049HCID 86663049, compoundYield 670%

Reagents, catalysts & solvents 2

HCID 6099591Rhodium(II) Octanoate DimerCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

1,2-Dichloroethane (30 mL) was added to a mixture of methyl 3-azido-6-bromo-2-(4-nitrophenyl)isonicotinate (6.5 g, 17 2 mmol), rhodium octanoate dimer (0.669 g, 0.859 mmol) and crushed 4A° molecular sieves (6.5 g). The reaction heated at 80° C. for 14 hr. The crude mixture was diluted with THF and filtered. The collected solid were then extracted with additional hot THF. The solvents were removed from the combined filtrates and the residue was suspended in methanol, filtered and air dried to leave methyl 2-bromo-7-nitro-5H-pyrido[3,2-b]indole-4-carboxylate (5.0 g, 13.4 mmol, 78% yield). MS (ESI) m/z 351.91 (M+H). 1H NMR (500 MHz, DMSO-d6) δ ppm 12.31 (1H, br. s.), 8.63 (1H, d, J=2.14 Hz), 8.45 (1H, d, J=8.55 Hz), 8.17 (1H, dd, J=8.55, 2.14 Hz), 8.08 (1H, s), 4.07 (3H, s).

Workup

  1. customcrushed 4A° molecular sieves (6.5 g)
  2. filtrationfiltered
  3. extractionThe collected solid were then extracted with additional hot THF
  4. customThe solvents were removed from the combined filtrates
  5. filtrationfiltered
  6. customair dried

Sources & evidence

ORD record
ord-4f2863107a6e4e00ae4350f3cfe2a6e5
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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