Water → [2-(6-chloro-8-nitro-9H-beta-carbolin-7-ylsulfanyl)-ethyl]-dimethyl-amine

HRID 12204

Reaction equation

HRID 12204 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:16]([O-:18])=[O:17])[C:14]=1F)[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1.Cl.[CH3:20][N:21]([CH3:25])[CH2:22][CH2:23][SH:24].C([Li])CCC.O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([N+:16]([O-:18])=[O:17])[C:14]=1[S:24][CH2:23][CH2:22][N:21]([CH3:25])[CH3:20])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

6

Reactant 4

HCID 962WaterHCID 25798Captamine HydrochlorideHCID 593375336-chloro-7-fluoro-8-nitro-9H-pyrido[3,4-b]indole2×HCID 178418339Butyllithium

Product 1

HCID 67166181[2-(6-chloro-8-nitro-9H-beta-carbolin-7-ylsulfanyl)-ethyl]-dimethyl-amineYield 84%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 25 ml round-bottom flask with magnetic stirrer was charged with 6-chloro-7-fluoro-8-nitro-9H-β-carboline (98 mg, 0.37 mmol) in 2 ml of anhydrous DMF. A second 10 ml round-bottom flask with magnetic stirrer was charged with 2-dimethylamino-ethanethiol hydrochloride (100 mg, 0.70 mmol) in 2 ml anhydrous DMF. To the resulting suspension was added n-butyllithium (0.43 ml of 1.6 M solution in hexanes, 0.69 mmol) via syringe and the mixture was stirred for 5 min at RT. Next, the thioanion solution was added via syringe to 6-chloro-7-fluoro-8-nitro-9H-β-carboline, and the resulting red solution was stirred at RT for 30 min. The reaction mixture was slowly added to a 5:1 mixture of H2O/saturated aqueous sodium bicarbonate (30 ml) and allowed to sit at RT for several hours. The resulting precipitated solid was collected via suction filtration and air-dried to afford 109 mg of [2-(6-chloro-8-nitro-9H-β-carbolin-7-ylsulfanyl)-ethyl]-dimethyl-amine as an orange solid (83%).

Workup

  1. stirringthe resulting red solution was stirred at RT for 30 min
  2. waitto sit at RT for several hours
  3. customThe resulting precipitated solid
  4. filtrationwas collected via suction filtration
  5. customair-dried

Sources & evidence

ORD record
ord-bc514ad0e3e84d83be2220180f062766
Source dataset
uspto-grants-2010_06
Patent number
US07727985B2

Linked notes

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