Water → 6-chloro-7-ethylsulfanyl-8-nitro-9H-beta-carboline

HRID 552202Notes

Reaction equation

HRID 552202 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.[S-:19][CH2:20][CH3:21].[Na+].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:19][CH2:20][CH3:21])[NH:11][C:10]1[CH:9]=[N:8][CH:7]=[CH:6][C:5]2=1

Participants

5

Reactant 3

HCID 962WaterHCID 4459711Sodium ethanethiolateHCID 593375336-chloro-7-fluoro-8-nitro-9H-pyrido[3,4-b]indole

Product 1

HCID 671657586-chloro-7-ethylsulfanyl-8-nitro-9H-beta-carbolineYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 25 ml round-bottom flask with a magnetic stirrer was charged with 6-chloro-7-fluoro-8-nitro-9H-β-carboline (102 mg, 0.38 mmol) in 5 ml of anhydrous DMF. To the resulting orange mixture at RT was slowly added sodium thioethoxide (80% pure, 69.7 mg, 0.66 mmol) in powder form. The reaction mixture was stirred at RT for 45 minutes, then added drop-wise to a 5:1 mixture of H2O/saturated sodium bicarbonate (30 ml). The resulting precipitated solid was collected by suction filtration, washed with 1:1 hexanes/diethyl ether (2×20 ml), and air-dried to afford 95.0 mg of 6-chloro-7-ethylsulfanyl-8-nitro-9H-β-carboline as an orange solid (79%). 1H-NMR (300 MHz, CD3OD, ppm) δ 8.91 (1H, s) 8.63 (1H, s) 8.42 (1H, d) 8.18 (1H, d) 3.04 (2H, q) 1.20 (3H, t). Retention Time (LC, formic acid standard method): 1.71 min. MS (M+H+): 308.

Workup

  1. customat RT
  2. additionadded drop-wise
  3. customThe resulting precipitated solid
  4. filtrationwas collected by suction filtration
  5. washwashed with 1:1 hexanes/diethyl ether (2×20 ml)
  6. customair-dried

Sources & evidence

ORD record
ord-37c37620826d43228448142efe8a7208
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

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