Dimethyl Sulfide → HCID 59239023, compound

HRID 1949126Notes

Reaction equation

HRID 1949126 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[C:9]([O:15][CH3:16])=[C:8]3[NH:17][C:18]4[CH:19]=[CH:20][C:21]([F:24])=[CH:22][C:23]=4[C:7]3=[CH:6][C:5]2=1.[H-].[Na+].Cl[CH2:28][C:29]#[N:30].S(C)[CH3:32].C[N:35]([CH:37]=O)C>C1COCC1>[F:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[N:17]([CH2:28][CH2:29][NH2:30])[C:8]1[C:9]([O:15][CH3:16])=[C:10]3[N:11]([CH2:32][CH2:37][NH2:35])[C:12]4[CH:13]=[CH:14][C:2]([F:1])=[CH:3][C:4]=4[C:5]3=[CH:6][C:7]2=1

Participants

7

Reactant 5

HCID 1068Dimethyl SulfideHCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 24758Sodium hydrideHCID 45138927HCID 45138927, compound

Product 1

HCID 59239023HCID 59239023, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,10-difluoro-6-methoxy-5,7-dihydroindolo[2,3-b]carbazole (1 equiv) in DMF (10 mL/mmol) was cooled in an ice-water bath under argon, and NaH (6 equiv, 60% in mineral oil) was added. The resultant mixture was stirred at 0-5° C. for 30 min and chloroacetonitrile was added. The cooling bath was removed and the reaction was warmed to RT and stirred for 2 h. The reaction was quenched with cold water, extracted ethyl acetate. The extract was washed three times with brine, dried over Na2SO4, filtered, and evaporated to give a solid, which was subjected to chromatography on silica gel. The di-nitrile substituted compound was dissolved in THF and cooled in an ice-water bath. Excess BH3.SMe2 was added to the solution and the resultant mixture was refluxed until reduction was complete (˜3 h), and then quenched with MeOH at 0-5° C. The solvent was evaporated and the residue was subjected to chromatography on silica gel to give 2,2′-(2,10-difluoro-6-methoxyindolo[2,3-b]carbazole-5,7-diyl)diethanamine (45% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.69 (s, 1H), 7.92 (dd, J=12.2, 3.4 Hz, 2H), 7.64 (dd, J=11.6, 5.6 Hz, 2H), 7.25 (td, J=12.4, 3.6 Hz, 2H), 4.55 (t, J=9.2 Hz, 4H), 3.96 (s, 3H), 2.89 (t, J=8.8 Hz, 4H); MS (ESI) m/z 409 (M+H)+.

Workup

  1. customThe cooling bath was removed
  2. customThe reaction was quenched with cold water
  3. extractionextracted ethyl acetate
  4. washThe extract was washed three times with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customto give a solid, which
  9. temperaturecooled in an ice-water bath
  10. custom(˜3 h)
  11. customquenched with MeOH at 0-5° C
  12. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a1bb06d53d2942dc9f4b47431c200cc9
Source dataset
uspto-grants-2013_03
Patent number
US08399502B2

Reaction notes

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