1,2-Dichloroethane → HCID 86663060, compound

HRID 2410837Notes

Reaction equation

HRID 2410837 reaction equation
ClCCCl.[N:5]([C:8]1[C:17]([C:18]2[CH:23]=[CH:22][C:21]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:20][CH:19]=2)=[N:16][C:15]([Br:30])=[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]>[Br:30][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]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH:22]=[CH:23][C:18]=3[C:17]=2[N:16]=1

Participants

5

Reactant 2

HCID 111,2-DichloroethaneHCID 86663059HCID 86663059, compound

Product 1

HCID 86663060HCID 86663060, compoundYield 1,040%

Reagents, catalysts & solvents 2

HCID 6099591Rhodium(II) Octanoate DimerCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
85 °C

Procedure

1,2-Dichloroethane (14 mL) was added to a mixture of methyl 3-azido-6-bromo-2-(4-morpholinophenyl)isonicotinate (4.66 g, 11 1 mmol), rhodium octanoate dimer (0.521 g, 0.669 mmol) and crushed 4A° molecular sieves (4.66 g) and this was heated at 85° C. for 26 hr. It was diluted with DCM, filtered, and the solid was washed with multiple portions of DCM. The solvent was removed from the combined filtrate and the residue was suspended in MeOH. The solid was collected by filtration, washed with MeOH, and dried to leave methyl 2-bromo-7-morpholino-5H-pyrido[3,2-b]indole-4-carboxylate (4.05 g, 10.4 mmol, 93% yield) as a yellow solid. MS (ESI) m/z 390.11 (M+H). 1H NMR (500 MHz, chloroform-d) δ ppm 9.43 (1H, br. s.), 8.20 (1H, d, J=8.85 Hz), 7.86 (1H, s), 7.00 (1H, dd, J=8.70, 1.68 Hz), 6.89 (1H, s), 4.06 (3H, s), 3.91-3.96 (4H, m), 3.32-3.37 (4H, m).

Workup

  1. customcrushed 4A° molecular sieves (4.66 g)
  2. filtrationfiltered
  3. washthe solid was washed with multiple portions of DCM
  4. customThe solvent was removed from the combined filtrate
  5. filtrationThe solid was collected by filtration
  6. washwashed with MeOH
  7. customdried

Sources & evidence

ORD record
ord-5fd786716e2c4ad8bc3b4039bf5399a8
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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