Dimethyl Sulfide → 1H-Pyrrolo(3,2-c)pyridine, 2,3-dihydro-6-chloro-

HRID 1475300Notes

Reaction equation

HRID 1475300 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][N:3]=1.S(C)C.C1COCC1>CO>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[CH2:6][CH2:7][NH:8][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 8028TetrahydrofuranHCID 125755166-Chloro-1H-pyrrolo[3,2-c]pyridine

Product 1

HCID 2118231H-Pyrrolo(3,2-c)pyridine, 2,3-dihydro-6-chloro-Yield 41.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under nitrogen, 6-chloro-5-aza indole (500 mg, 3.29 mmol) was dissolved in 2.0 M BH3.SMe2 in THF (6.6 mL, 13.16 mmol) and heated gently to 68° C. for 2 h. After cooling to ambient temperature, MeOH (6.0 mL) was added slowly over 20 min. Once bubbling had stopped, the reaction was heated to 68° C. for 30 min, then cooled to ambient temperature and concentrated in vacuo. Chromatography on silica gel (gradient elution, 0-60% EtOAc/petrol), gave the title compound (209 mg, 41%) as colourless oil. 1H NMR (CDCl3): 7.86 (1H, s), 6.43 (1H, s), 4.33 (1H, s), 3.80-3.65 (2H, m), 3.05 (2H, t).

Workup

  1. customOnce bubbling
  2. temperaturethe reaction was heated to 68° C. for 30 min
  3. temperaturecooled to ambient temperature
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-188f0803b47042c0967475b6a4864e4e
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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