Hydrochloric Acid → HCID 58382170, compound

HRID 1627994Notes

Reaction equation

HRID 1627994 reaction equation
[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[N:10]([Si](C(C)C)(C(C)C)C(C)C)[CH:11]=[C:12]([CH2:13][CH3:14])[C:3]=12.Cl>O1CCOCC1>[Cl:1][C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[C:12]([CH2:13][CH3:14])[C:3]=12

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58382001HCID 58382001, compound

Product 1

HCID 58382170HCID 58382170, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-Chloro-3-ethyl-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1.48 g, 4.05 mmol) in 1,4-dioxane (15 mL) was treated with HCl (4.0 N in 1,4-dioxane, 2.0 mL, 8.1 mmol) then the mixture was stirred for about 16 h at rt. The solvents were evaporated then the material was suspended in Et2O (15 mL) then the solids were collected by filtration and dried under reduced pressure overnight to give 4-chloro-3-ethyl-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (0.762 g, 90%): LC/MS (Table 2, Method a) Rt=2.21 min; MS m/z 209 (M+H)+.

Workup

  1. customThe solvents were evaporated
  2. filtrationthe solids were collected by filtration
  3. customdried under reduced pressure overnight

Sources & evidence

ORD record
ord-ba8b017322574adfb622f12e35436d29
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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