Bromine → HCID 67485364, compound

HRID 1809602Notes

Reaction equation

HRID 1809602 reaction equation
[CH:1]1([O:6][C:7]2[C:8]([N+:13]([O-])=O)=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Br:16]Br>C(O)(=O)C.[Zn]>[Br:16][C:11]1[CH:12]=[C:7]([O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:8]([NH2:13])=[N:9][CH:10]=1

Participants

5

Reactant 2

HCID 24408BromineHCID 67485831HCID 67485831, compound

Product 1

HCID 67485364HCID 67485364, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

3-(cyclopentyloxy)-2-nitropyridine (8.2 g, 39.3 mmol) in acetic acid (90 mL) was cooled in a water bath. Zn dust (10 microns) (12.9 g, 197 mmol) was slowly added in portions over 15 minutes and the reaction stirred for an additional 30 minutes. The solution was filtered over celite and the solids were rinsed with DCM. The filtrate was concentrated to about 90 mL of acetic acid. To this solution was added bromine (2.0 mL, 39.3 mmol) in dropwise manner. After 15 minutes, the material was concentrated and neutralized with saturated NaHCO3 solution. The material was extracted with dichloromethane and the organic layer was dried, and concentrated. Flash chromatography gave 5-bromo-3-(cyclopentyloxy)pyridin-2-amine (5.26 g, 52% yield) as a yellow solid.

Workup

  1. filtrationThe solution was filtered over celite
  2. washthe solids were rinsed with DCM
  3. concentrationThe filtrate was concentrated to about 90 mL of acetic acid
  4. waitAfter 15 minutes
  5. concentrationthe material was concentrated
  6. extractionThe material was extracted with dichloromethane
  7. customthe organic layer was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-60c30bb77d6d4911832450c641cb4c1d
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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