Cesium carbonate → Methyl 6-(((4-fluorobenzyl)amino)methyl)picolinate

HRID 1889723Notes

Reaction equation

HRID 1889723 reaction equation
CS(O[CH2:6][C:7]1[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=1)(=O)=O.[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH2:23])=[CH:20][CH:19]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[F:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][NH:23][CH2:6][C:7]2[N:12]=[C:11]([C:13]([O:15][CH3:16])=[O:14])[CH:10]=[CH:9][CH:8]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 673264-FluorobenzylamineHCID 54451634Methyl 6-((methylsulfonyloxy)methyl)picolinate

Product 1

HCID 58531465Methyl 6-(((4-fluorobenzyl)amino)methyl)picolinateYield 31.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 6-((methylsulfonyloxy)methyl)picolinate (0.4 g, 1.63 mmol) in CH3CN (15 mL) were added 4-fluorobenzylamine (0.75 mL, 6.52 mmol) and Cs2CO3 (0.8 g, 2.45 mmol). The reaction mixture was stirred at rt for 4 h, filtered and the filtrate solution was concentrated in vacuo. The residue was purified by preparative HPLC. Fractions containing the desired product were combined and concentrated to give the desired compound (140 mg, 31%) as an oil. 1H NMR (CDCl3) δ 8.02 (d, J=8.0 Hz, 1H), 7.81 (t, J=8.0 Hz, 1H), 7.59 (d, J=8.0 Hz, 1H), 7.35-7.31 (m, 2H), 7.04-6.99 (m, 2H), 4.02 (s, 2H), 3.99 (s, 3H), 3.82 (s, 2H). MS (ESI): 275.1 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate solution was concentrated in vacuo
  3. customThe residue was purified by preparative HPLC
  4. additionFractions containing the desired product
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7f29d706f218429786777c700978fa5b
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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