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

HRID 911893Notes

Reaction equation

HRID 911893 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 25 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. customwas evaporated
  2. customThe organic phase was separated
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluted with 1-3% methanol/dichloromethane

Sources & evidence

ORD record
ord-b0bf5c8e94bd4df2a62a93d32f1d5877
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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