Water → HCID 9879865, compound

HRID 1359140Notes

Reaction equation

HRID 1359140 reaction equation
[C:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([NH2:18])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:19](Cl)([CH3:22])(=[O:21])=[O:20].C(N(CC)CC)C.O>ClCCl>[C:1]([N:9]1[C:17]2[C:12](=[CH:13][C:14]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:16]=2)[CH:11]=[CH:10]1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 9856121HCID 9856121, compound

Product 1

HCID 9879865HCID 9879865, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-benzoyl-5-amino-1H-indole (25 mg, 0.106 mmol) was dissolved in dichloromethane (1.0 ml) at room temperature and mesyl chloride (0.01 ml. 0.116 mmol) and triethylamine (0.016 ml, 0.115 mmol) were added. The solution was stirred at room temperature for 30 minutes to complete the reducing reaction. After pouring water (2 ml), dichloromethane layer was separated, washed with brine, dried over anhydrous magnesium sulfate and then, purified through flash column chromatography (an eluent:ethyl acetate/n-hexane=1/2, v/v). As a result, the present compound (20 mg, productive yield 60%) was obtained.

Workup

  1. customthe reducing reaction
  2. customwas separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. custompurified through flash column chromatography (an eluent
  6. customAs a result, the present compound (20 mg, productive yield 60%) was obtained

Sources & evidence

ORD record
ord-2b8866722ecd4d6bb9ee96da46234cd2
Source dataset
uspto-grants-2003_07
Patent number
US06599929B2

Reaction notes

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