Perchloric Acid → HCID 59699856, compound

HRID 729808Notes

Reaction equation

HRID 729808 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:10]OC)[C:5]([NH2:8])=[N:6][CH:7]=1.Cl(O)(=O)(=O)=O>O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9]([CH:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:10][NH:8][C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 24247Perchloric AcidHCID 67061219HCID 67061219, compound

Product 1

HCID 59699856HCID 59699856, compoundYield 67.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 5-bromo-3-(1-cyclopentyl-2-methoxy-vinyl)-pyridin-2-ylamine (116.9 mg, 0.39 mmol) and perchloric acid (0.11 mL) in dioxane (1 mL) was heated at 80° C. for 2 hrs. Solvents were evaporated and the residue was washed with a solution of 2M sodium carbonate (5 mL). A precipitate was formed and filtered off. It was washed with water and dried to afford the product 5-bromo-3-cyclopentyl-1H-pyrrolo[2,3-b]pyridine (69.8 mg, 67% yield) as a brown solid. MS: m/z 265/266 [MH+].

Workup

  1. customSolvents were evaporated
  2. washthe residue was washed with a solution of 2M sodium carbonate (5 mL)
  3. customA precipitate was formed
  4. filtrationfiltered off
  5. washIt was washed with water
  6. customdried

Sources & evidence

ORD record
ord-d6ffca41ed0942c985ed900e925c29a1
Source dataset
uspto-grants-2009_09
Patent number
US07582637B2

Reaction notes

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