Lithium → 4-(2-Chlorophenyl)-9-hydroxy-6-[3-(methylsulfanyl)propyl]pyrrolo[3,4-c]carbazole-1,3(2h,6h)-dione

HRID 11100

Reaction equation

HRID 11100 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:14]3[C:25](=[O:29])[NH:26][C:27](=[O:28])[C:13]=3[C:12]=2[C:11]2[CH:10]=[C:9]([OH:30])[CH:8]=[CH:7][C:6]1=2.[Li].[Li][S:33][CH3:34]>O1CCOCC1.O>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:15]1[C:14]2[C:25](=[O:29])[NH:26][C:27](=[O:28])[C:13]=2[C:12]2[C:11]3[CH:10]=[C:9]([OH:30])[CH:8]=[CH:7][C:6]=3[N:5]([CH2:4][CH2:3][CH2:2][S:33][CH3:34])[C:17]=2[CH:16]=1

Participants

6

Reactant 3

HCID 3028194LithiumHCID 219805126-(3-Bromopropyl)-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneHCID 178418898HCID 178418898, compound

Product 1

HCID 117445124-(2-Chlorophenyl)-9-hydroxy-6-[3-(methylsulfanyl)propyl]pyrrolo[3,4-c]carbazole-1,3(2h,6h)-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of the bromide (58) (60.0 mg, 0.124 mmol) prepared as described in example 172 and lithium thiomercaptide (13 mg, 0.2481 mmol) in p-dioxane (5 mL) was refluxed for 16 h. A further 10 mg of LiSMe was added and refluxing was continued for a further 9 h. The mixture was diluted with water, extracted with ethyl acetate. The organic layer was dried, the drying agent was removed and the solution was concentrated to drynessto give the sulfide (130 directly (47.1 mg, 84%) which crystallised from ethyl acetate/petroleum ether as an orange powder, mp 218–220° C. 1H NMR δ [(CD3)2SO] 11.07 (br s, 1H), 9.39 (br s, 1H), 8.39 (d, J=2.4 Hz, 1H), 7.80 (s, 1H), 7.61–7.56 (m, 2H), 7.53–7.43 (m, 3H), 7.15 (dd, J=8.8, 2.4 Hz, 1H), 4.52 (t, J=6.9 Hz, 2H), 2.45 (t, J=7.0 Hz, 2H), 2.01 (m, 2H), 2.00 (s, 3H). FABMS found [M+H]+: 453.0840, 451.0859. C24H20ClN2O3S requires 453.0854, 451.0883.

Workup

  1. customprepared
  2. temperaturewas refluxed for 16 h
  3. temperaturerefluxing
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was dried
  6. customthe drying agent was removed
  7. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-abff0e57043e4cab848989dfd590d22d
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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