5-Methoxy-3-pyridinecarboxaldehyde → HCID 68053719, compound

HRID 1048938Notes

Reaction equation

HRID 1048938 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=O)[CH:6]=[N:7][CH:8]=1.[F:11][C:12]1[CH:13]=[C:14]([NH:19][CH3:20])[C:15]([NH2:18])=[CH:16][CH:17]=1>CN(C=O)C.O.C(OCC)(=O)C>[F:11][C:12]1[CH:17]=[CH:16][C:15]2[N:18]=[C:9]([C:5]3[CH:6]=[N:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[N:19]([CH3:20])[C:14]=2[CH:13]=1

Participants

6

Reactant 2

HCID 109755495-Methoxy-3-pyridinecarboxaldehydeHCID 184572834-Fluoro-N2-methyl-1,2-benzenediamine

Product 1

HCID 68053719HCID 68053719, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 5-methoxypyridine-3-carbaldehyde (0.052 g, 0.378 mmol) in DMF (1.89 mL) were added the title compound from Example 1 Step B (0.053 g, 0.38 mmol) and Na2S2O5 (0.288 g, 1.51 mmol). The resulting mixture was stirred at 120° C. overnight, then cooled to room temperature and diluted with water and ethyl acetate. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. Purification by flash chromatography on silica gel (50% ethyl acetate in hexanes, then 100% ethyl acetate) provided the title compound: LCMS m/z 258.17 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 8.56 (d, J=1.6 Hz, 1 H), 8.46 (d, J=2.9 Hz, 1 H), 7.66 (dd, J=8.6, 4.8 Hz, 1 H), 7.65 (t, J=2.1, 2.1 Hz, 1 H), 7.12-7.06 (m, 2 H), 3.95 (s, 3 H), 3.88 (s, 3 H).

Workup

  1. temperaturecooled to room temperature
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel (50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f72b5d97ba9245de8e13dbd2f23445c0
Source dataset
uspto-grants-2016_07
Patent number
US09382226B2

Reaction notes

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