Bromine → 4-(4-Methoxybenzylthio)-5-bromopyridin-2-amine

HRID 911054Notes

Reaction equation

HRID 911054 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]([CH2:7][S:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)=[CH:5][CH:4]=1.[Br:18]Br>C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8][C:9]2[C:14]([Br:18])=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 666179194-(4-Methoxybenzylthio)pyridine-2-amine

Product 1

HCID 666178114-(4-Methoxybenzylthio)-5-bromopyridin-2-amineYield 54.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-(4-methoxybenzylthio)pyridine-2-amine (2.4 g, 9.7 mmol) was dissolved in acetic acid (30 mL). Bromine (1M in AcOH, 9.8 ml, 9.8 mmol) was added dropwise at ambient temperature and the reaction stirred for 30-minutes. The solution was concentrated and the residue was neutralized with saturated NaHCO3 solution. The solution was extracted with EtOAc and the organic layer was dried and concentrated. The residue was purified by flash chromatography (70% EtOAc/hexanes) to obtain the desired product (1.71 g, 54% yield) as a yellow solid.

Workup

  1. concentrationThe solution was concentrated
  2. extractionThe solution was extracted with EtOAc
  3. customthe organic layer was dried
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0cbed290ebdc47dbbc5dcf4d65e96e92
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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