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

HRID 552205

Reaction equation

HRID 552205 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%). LCMS (ammonium acetate standard method) retention time=1.35 min. (M+=351; M−=349). 1H-NMR (300 MHz, CD3OD, ppm) δ 8.92 (1H, d, J=1.0 Hz) 8.66 (1H, s) 8.43 (1H, d) 8.19 (1H, dd) 3.18-3.13 (2H, m) 2.57-2.52 (2H, m) 2.21 (6H, s).

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-bb229da44ac841bca8c83e4e1953afaf
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Linked notes

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