HCID 67252931, compound → HCID 67252307, compound

HRID 2042057Notes

Reaction equation

HRID 2042057 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([N:13](CC3C=CC=CC=3)[CH3:14])[CH:8]=2)=[C:4]([F:24])[CH:3]=1>CO.[Pd]>[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][CH3:14])[CH:8]=2)=[C:4]([F:24])[CH:3]=1

Participants

4

Reactant 1

HCID 67252931HCID 67252931, compound

Product 1

HCID 67252307HCID 67252307, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 4-(4-amino-2-fluorophenoxy)-N-benzyl-N-methylpyridin-2-amine (1.0 g, 3.1 mmol) in MeOH (10 mL) was added 10% Pd/C (0.25 g, 0.23 mmol). The reaction was stirred under a H2 atmosphere (50 psi) at 75° C. for 12 h. The reaction mixture was filtered, concentrated under reduced pressure and purified by reverse phase prep-HPLC to provide 4-(4-amino-2-fluorophenoxy)-N-methylpyridin-2-amine (560 mg, 78% yield). 1H NMR (400 MHz, DMSO-d6) δ 7.80 (d, J=5.6 Hz, 1H), 6.90 (t, J=9.0 Hz, 1H), 6.40-6.45 (m, 3H), 6.06 (dd, J=8.0, 2.8 Hz, 1H), 5.73 (d, J=2.8 Hz, 1H), 5.37 (s, 2H), 2.68 (d, J=4.8 Hz, 3H); MS (ESI) m/z: (M+H+): 234.2.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. custompurified by reverse phase prep-HPLC

Sources & evidence

ORD record
ord-c8e9cf28aa7d4fe3ac6e2383db6797d6
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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