1,2-Dichloroethane → HCID 86663038, compound

HRID 2410785Notes

Reaction equation

HRID 2410785 reaction equation
ClCCCl.[N:5]([C:8]1[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH:24]=[O:25])[CH:19]=2)=[N:16][C:15]([Br:26])=[CH:14][C:9]=1[C:10]([O:12][CH3:13])=[O:11])=[N+]=[N-]>CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.CCCCCCCC(O)=O.[Rh].[Rh].C1COCC1>[Br:26][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]=[CH:21][C:20]([CH:24]=[O:25])=[CH:19][C:18]=3[C:17]=2[N:16]=1

Participants

5

Reactant 2

HCID 111,2-DichloroethaneHCID 86663037HCID 86663037, compound

Product 1

HCID 86663038HCID 86663038, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6099591Rhodium(II) Octanoate DimerCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

1,2-Dichloroethane (1.7 mL) was added to a mixture of methyl 3-azido-6-bromo-2-(3-formylphenyl)isonicotinate (903 mg, 2.50 mmol), rhodium octanoate dimer (156 mg, 0.20 mmol) and crushed 4A° molecular sieves (0.9 gm) in an flask. This was heated at 80° C. for 18 hr. The reaction was diluted THF and filtered. The collected solid was washed with multiple portions of boiling THF to complete extraction of the product. The solvent was removed from the combined filtrates, the residue was suspended in MeOH, and the product was collected by filtration. This left methyl 2-bromo-8-formyl-5H-pyrido[3,2-b]indole-4-carboxylate (484 mg, 1.45 mmol, 58% yield) as a grey solid. MS (ESI) m/z 334.91 (M+H). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.25 (1H, s), 10.12 (1H, s), 8.80 (1H, s), 8.11 (1H, d, J=9.32 Hz), 7.98 (1H, s), 7.88(1H, d, J=8.56 Hz), 3.33 (3H, s).

Workup

  1. customcrushed 4A° molecular sieves (0.9 gm) in an flask
  2. filtrationfiltered
  3. washThe collected solid was washed with multiple portions of boiling THF
  4. extractionextraction of the product
  5. customThe solvent was removed from the combined filtrates
  6. filtrationthe product was collected by filtration

Sources & evidence

ORD record
ord-2fc03bbfdaa848f9930a8b2825cbc5be
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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