HCID 86619668, compound → HCID 67253302, compound

HRID 2042037Notes

Reaction equation

HRID 2042037 reaction equation
[F:1][C:2]1[CH:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([N:16](OC)[CH3:17])[CH:11]=2)[CH:6]=[CH:5][C:3]=1[NH2:4]>CO.[Pd]>[NH2:4][C:3]1[CH:5]=[CH:6][C:7]([O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([NH:16][CH3:17])[CH:11]=2)=[CH:8][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 86619668HCID 86619668, compound

Product 1

HCID 67253302HCID 67253302, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-fluoro-4-(2-(methoxy(methyl)amino)pyridine-4-yloxy)aniline (2.0 g, 7.6 mmol) and 10% Pd/C (200 mg, 0.18 mmol) in MeOH (15 mL) was stirred under a H2 atmosphere (50 psi) at RT for 48 h. The mixture was filtered through Celite® and the cake was washed with MeOH. The filtrate was concentrated to afford 4-(4-amino-3-fluorophenoxy)-N-methylpyridin-2-amine (1.2 g, 68% yield). 1H NMR (DMSO-d6) δ 7.86 (d, J=6.3 Hz, 1H), 6.82-6.69 (m, 3H), 6.18 (dd, J=6.0, 2.1 Hz, 1H), 5.84 (d, J=2.1 Hz, 1H), 5.41 (br s, 1H), 3.62 (s, 2H), 2.84 (d, J=3.0 Hz, 3H); MS (ESI) m/z: 234.2 (M+H+).

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washthe cake was washed with MeOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d90179142d3f4c66a7b7978fa47ed5fe
Source dataset
uspto-grants-2013_11
Patent number
US08586565B2

Reaction notes

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