Sulfur → HCID 10244226, compound

HRID 1085439Notes

Reaction equation

HRID 1085439 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:18][C:17]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([F:19])[CH:15]=3)[NH:10][C:9]=2[CH2:8][NH:7]1)=[O:5])[CH3:2].[S]>C1(C)C(C)=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][C:14]([F:19])=[CH:13][CH:12]=3)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 5362487SulfurHCID 13037301HCID 13037301, compound

Product 1

HCID 10244226HCID 10244226, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

720 mg of 6-fluoro-1,2,3,4-tetrahydro-β-carbolin-3-carboxylic acid ethyl ester and 130 mg of dry sulphur are heated to boiling under nitrogen in 5 ml of xylene. After cessation of dehydrogenation (about 20 hours, thin-layer chromatography check), the solution is concentrated by evaporation in vacuo, and the residue chromatographed on silica gel with chloroform ethanol (95:5). 300 mg of 6-fluoro-β-carbolin-3-carboxylic acid ethyl ester of melting point 284° C. (decomposition) is obtained. After reaction with hydrochloric acid, the hydrochloride which melts at 295° C., with decomposition, is obtained.

Workup

  1. concentrationAfter cessation of dehydrogenation (about 20 hours, thin-layer chromatography check), the solution is concentrated by evaporation in vacuo
  2. customthe residue chromatographed on silica gel with chloroform ethanol (95:5)

Sources & evidence

ORD record
ord-db56a119b3c84821b18350420579643c
Source dataset
uspto-grants-1991_04
Patent number
US05010077

Reaction notes

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