Hydrochloric Acid → HCID 9901549, compound

HRID 1359139Notes

Reaction equation

HRID 1359139 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([N+:16]([O-])=O)=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1.C([O-])=O.[NH4+].[S:25](Cl)([CH3:28])(=[O:27])=[O:26].Cl>O1CCCC1.CO.[Pd].C(N(CC)CC)C>[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([NH:16][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:13][CH:14]=3)[CH:9]=[CH:8]2)=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 2723923Ammonium formateHCID 9856675HCID 9856675, compound

Product 1

HCID 9901549HCID 9901549, compoundYield 51%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
30 °C

Procedure

1-(4-fluoro-benzyl)-5-nitro-1H-indole (50 mg, 0.16 mmol) was dissolved in tetrahydrofuran (1 ml) and methanol (1 ml), and ammonium formate of an excess amount and palladium/carbon (10%) of a catalytic amount were added. The solution was stirred at around 30° C. for 1 hour to complete the reduction, filtered through celite, concentrated under reduced pressure, dissolved again in dichloromethane (10 ml), and then washed with water and brine. After drying the resulting solution over anhydrous magnesium sulfate, dichloromethane solution containing amine compound (1-(4-fluoro-benzyl)-5-amino-1H-indole) was obtained. Mesyl chloride (0.012 ml, 0.16 mmol) and triethylamine (0.022 ml, 0.16 mm) were added to the above obtained solution and stirred at room temperature for 2 hours to complete the reaction. After adding 2N-hydrochloric acid solution (10 ml) to separate layers, dichloromethane solution was induced, washed with water and brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then triturated with isooctane and isopropyleter. As a result, the present compound (30 mg, productive yield 51%) was obtained as a solid.

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated under reduced pressure
  3. dissolutiondissolved again in dichloromethane (10 ml)
  4. washwashed with water and brine
  5. dry with materialAfter drying the resulting solution over anhydrous magnesium sulfate, dichloromethane solution
  6. additioncontaining amine compound (1-(4-fluoro-benzyl)-5-amino-1H-indole)
  7. customwas obtained
  8. stirringstirred at room temperature for 2 hours
  9. customthe reaction
  10. customto separate layers, dichloromethane solution
  11. washwashed with water and brine
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customtriturated with isooctane and isopropyleter
  15. customAs a result, the present compound (30 mg, productive yield 51%) was obtained as a solid

Sources & evidence

ORD record
ord-4da917e49590410cad605bd60305f0b0
Source dataset
uspto-grants-2003_07
Patent number
US06599929B2

Reaction notes

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