Dichloromethane → HCID 68846701, compound

HRID 1784876Notes

Reaction equation

HRID 1784876 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([SH:11])[CH:7]=[C:8]([Cl:10])[CH:9]=1.Cl.Cl[CH2:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.C(Cl)Cl>O.C(O)C>[Cl:3][C:4]1[CH:5]=[C:6]([S:11][CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:7]=[C:8]([Cl:10])[CH:9]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 233943-(Chloromethyl)pyridine hydrochlorideHCID 27360963,5-Dichlorobenzenethiol

Product 1

HCID 68846701HCID 68846701, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Sodium hydroxide (0.154 g. 3.85 mmol) in 2 mL water was added to 3,5-dichloro-benzenethiol (0.328 g, 1.83 mmol) in 5 mL of ethanol. After 10 min stirring, 3-chloromethyl-pyridine hydrochloride (0.301 g, 1.83 mmol) in 2 mL water was added slowly. The resulting reaction mixture was stirred at room temperature overnight. Methylene chloride was added to the reaction mixture. The organic phase was washed with saturated aqueous sodium bicarbonate solution and brine. After removal of the solvent, the crude product was purified with flash chromatography to give 0.470 g (95% yield) of 3-(3,5-dichloro-phenylsulfanylmethyl)-pyridine. This compound was converted to N-[3-(1H-indol-4-yl)-5-(pyridin-3-ylmethylsulfanyl)-phenyl]-acetamide as described in Example 35. 1H NMR (400 MHz, CD3OD): δ 8.42 (s, 1H), 8.35 (d, J=4.7 Hz, 1H), 7.79 (d, J=7.8 Hz, 1H), 7.66 (s, 2H), 7.38-7.31 (m, 2H), 7.27-7.23 (m, 2H), 7.13 (t, J=7.7 Hz, 1H), 6.97 (d, J=7.2 Hz, 1H), 6.44 (d, J=3.1 Hz, 1H), 4.20 (s, 2H), 2.12 (s, 3H).

Workup

  1. customThe resulting reaction mixture
  2. stirringwas stirred at room temperature overnight
  3. washThe organic phase was washed with saturated aqueous sodium bicarbonate solution and brine
  4. customAfter removal of the solvent
  5. customthe crude product was purified with flash chromatography

Sources & evidence

ORD record
ord-b64c4dc4464f4057aa95327d0707b89a
Source dataset
uspto-grants-2009_03
Patent number
US07504401B2

Reaction notes

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