Dimethyl Sulfoxide → HCID 74221171, compound

HRID 718825Notes

Reaction equation

HRID 718825 reaction equation
[H-].[Na+].CS(C)=O.[I-].[CH3:8][S+](C)(C)=O.[CH2:13]([C@@:15]12[CH2:39][CH2:38][C:37](=[O:40])[CH2:36][C@H:16]1[CH2:17][CH2:18][CH2:19][C:20]1[C:21]2=[CH:22][C:23]2[CH:24]=[N:25][N:26]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[C:27]=2[CH:28]=1)[CH3:14]>C1COCC1>[CH2:13]([C@@:15]12[CH2:39][CH2:38][C@@:37]3([CH2:8][O:40]3)[CH2:36][C@H:16]1[CH2:17][CH2:18][CH2:19][C:20]1[C:21]2=[CH:22][C:23]2[CH:24]=[N:25][N:26]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[C:27]=2[CH:28]=1)[CH3:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 86722329HCID 86722329, compound

Product 1

HCID 74221171HCID 74221171, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

Sodium hydride (60 wt % in oil, 0.023 g, 0.967 mmol) was added carefully to a flask containing about 3 mL DMSO then heated to about 65° C. for about 30 min. The reaction was cooled to rt then diluted with 2 mL THF. The reaction was further cooled in an ice water bath and trimethylsulfoxonium iodide (0.213 g, 0.967 mmol) was added in one portion and stirred about 15 min. (4aR,12bR)-12b-ethyl-9-(4-fluorophenyl)-1,4,4a,5,6,7,9,12b-octahydrobenzo[6,7]cyclohepta[1,2-f]indazol-3 (2H)-one (9, R1=4-Fluorophenyl, R2=Ethyl) (0.182, 0.483 mmol) in 2 mL THF was introduced via syringe and allowed to warm to rt over about 18 hrs. THF was removed in vacuo and the residue was diluted with 15 mL water and extracted with EtOAc (15 mL×3). The combined organics were washed with sat. aq. NaCl. The organic layer was dried over MgSO4 filtered and concentrated to a crude viscous oil.

Workup

  1. temperatureThe reaction was cooled to rt
  2. temperatureThe reaction was further cooled in an ice water bath
  3. additionwas introduced via syringe
  4. temperatureto warm to rt over about 18 hrs
  5. customTHF was removed in vacuo
  6. additionthe residue was diluted with 15 mL water
  7. extractionextracted with EtOAc (15 mL×3)
  8. washThe combined organics were washed with sat. aq. NaCl
  9. dry with materialThe organic layer was dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated to a crude viscous oil

Sources & evidence

ORD record
ord-85018b16b35e4850bc9e9f2edb18ffba
Source dataset
uspto-grants-2015_11
Patent number
US09193744B2

Reaction notes

Loading…