Bromine → 3-(2-Bromo-5-morpholinophenoxy)pyridin-2-amine

HRID 1806141Notes

Reaction equation

HRID 1806141 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[C:9]([CH:18]=[CH:19][CH:20]=2)[O:10][C:11]2[C:12]([NH2:17])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH2:3][CH2:2]1.[Br:21]Br>C(O)(=O)C>[Br:21][C:18]1[CH:19]=[CH:20][C:7]([N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)=[CH:8][C:9]=1[O:10][C:11]1[C:12]([NH2:17])=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 669950653-(3-Morpholinophenoxy)pyridin-2-amine

Product 1

HCID 669953443-(2-Bromo-5-morpholinophenoxy)pyridin-2-amineYield 77.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In a 250 mL round-bottom flask, 3-(3-morpholinophenoxy)pyridin-2-amine (0.720 g, 2.654 mmol) was dissolved in mL of acetic acid and Bromine (2.654 mL, 2.654 mmol) (1M in AcOH) was added slowly. After agitating for 1 hour the mixture was evaporated and the residue was distributed between dichloromethane and sodium bicarbonate solution. The organic phase was separated and evaporated. The residue was purified by column chromatography on silica gel, eluted with 1-3% methanol/dichloromethane to give the title compound (0.72 g, 77%) as white solid.

Workup

  1. additionwas added slowly
  2. customwas evaporated
  3. customThe organic phase was separated
  4. customevaporated
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluted with 1-3% methanol/dichloromethane

Sources & evidence

ORD record
ord-10455246271b41279d4b568d2cb33064
Source dataset
uspto-grants-2013_01
Patent number
US08354540B2

Reaction notes

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