Dimethyl Sulfide → 1-(Phenylsulfonyl)-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline

HRID 1096483Notes

Reaction equation

HRID 1096483 reaction equation
S(C)C.[C:4]1([S:10]([N:13]2[C:23]3[C:24]4[C:15]([CH2:16][NH:17][C:18](=O)[C:19]=4[CH:20]=[CH:21][CH:22]=3)=[CH:14]2)(=[O:12])=[O:11])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C1COCC1>[C:4]1([S:10]([N:13]2[C:23]3[C:24]4[C:15]([CH2:16][NH:17][CH2:18][C:19]=4[CH:20]=[CH:21][CH:22]=3)=[CH:14]2)(=[O:12])=[O:11])[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 1068Dimethyl Sulfide2×HCID 667864451-(Phenylsulfonyl)-3,4-dihydropyrrolo[4,3,2-de]isoquinolin-5(1H)-one

Product 1

HCID 250721821-(Phenylsulfonyl)-1,3,4,5-tetrahydropyrrolo[4,3,2-de]isoquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

SMe2 (205 μL, 2.2 mmol) was added dropwise over 5 min. to a refluxing mixture of 1-(phenylsulfonyl)-3,4-dihydropyrrolo[4,3,2-de]isoquinolin-5(1H)-one, Intermediate 2, (225 mg, 0.72 mmol) in dry THF (10 mL) with continuous reflux for 2.5 h. Additional two portions BH3:SMe2 (100 μL×2) were added (2.5 h reflux between the additions). Reflux was continued for 5 h after the last addition, then room temperature over night. The reaction was quenched by addition of HCl in MeOH (1.25 M, 4 mL) and reflux 1 h. The solvent was evaporated and the crude mixture was extracted with DCM (×2) and sat. Na2CO3(aq). The organic layers were combined, dried and concentrated. Purification was performed by flash column chromatography (3-5% MeOH in DCM) which gave 66 mg of the title compound as a beige solid. MS m/z 299 [M+H]+.

Workup

  1. temperaturewith continuous reflux for 2.5 h
  2. temperaturereflux between the additions)
  3. temperatureReflux
  4. additionafter the last addition
  5. waitroom temperature over night
  6. customThe reaction was quenched by addition of HCl in MeOH (1.25 M, 4 mL)
  7. temperaturereflux 1 h
  8. customThe solvent was evaporated
  9. extractionthe crude mixture was extracted with DCM (×2) and sat. Na2CO3(aq)
  10. customdried
  11. concentrationconcentrated
  12. customPurification

Sources & evidence

ORD record
ord-7f3e8dce36204f0cb4b1dfd235aa1897
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

Loading…