Water → HCID 59843198, compound

HRID 2196580Notes

Reaction equation

HRID 2196580 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[O:11][CH3:12])=O.[NH2:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([Br:21])=[CH:16][N:15]=1.O>C(O)C>[Br:21][C:17]1[CH:18]=[C:19]([CH3:20])[C:14]2[N:15]([CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[O:11][CH3:12])[N:13]=2)[CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 123440Bromomethyl 2-methoxyphenyl ketoneHCID 1379342-Amino-5-bromo-3-methylpyridine

Product 1

HCID 59843198HCID 59843198, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2-bromo-2′-methoxyacetophenone (0.500 g, 2.183 mmol) and 2-amino-5-bromo-3-methylpyridine (0.408 g, 2.183 mmol) in ethanol (8 mL) was heated to 80° C. for 16 hours in a pressure vessel. A yellow thick precipitate formed. Water was added and the solid was extracted with ethyl acetate (some DCM and MeOH were added to help in the dissolution). The organic extracts were then washed with brine, dried over Na2SO4, filtered and concentrated and the residue was purified by silica gel chromatography (Biotage SNAP 100 g, 10 to 20% ethyl acetate in hexanes) to give 220 (0.375 g, 1.182 mmol, 54.2% yield) as a white solid. LRMS (ESI): calc. 316.02 found 317.1 (MH)+.

Workup

  1. customA yellow thick precipitate formed
  2. extractionthe solid was extracted with ethyl acetate (some DCM and MeOH
  3. additionwere added
  4. dissolutionto help in the dissolution)
  5. washThe organic extracts were then washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customthe residue was purified by silica gel chromatography (Biotage SNAP 100 g, 10 to 20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-131aaa0041c0475f9ee6cf44eb798276
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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