Methyl 5-chloro-6-cyano-2-(3-fluorophenyl)nicotinate → Methyl 6-(aminomethyl)-5-chloro-2-(3-fluorophenyl)nicotinate

HRID 717817Notes

Reaction equation

HRID 717817 reaction equation
[Cl:1][C:2]1[C:3]([C:19]#[N:20])=[N:4][C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8]>CO.[Pd]>[NH2:20][CH2:19][C:3]1[C:2]([Cl:1])=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[N:4]=1

Participants

4

Reactant 1

HCID 58515932Methyl 5-chloro-6-cyano-2-(3-fluorophenyl)nicotinate

Product 1

HCID 58515976Methyl 6-(aminomethyl)-5-chloro-2-(3-fluorophenyl)nicotinate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Methyl 5-chloro-6-cyano-2-(3-fluorophenyl)nicotinate (1.3 g, 4.5 mmol) was stirred in methanol (60 mL), and 5% palladium on carbon (1.0 g) was added. The mixture was degassed three times and placed under a balloon pressure of hydrogen for 4 hours. A solution of 0.5 M sodium methoxide in methanol (45 mL) was added and the mixture was filtered through celite. The filtrates were evaporated and the residue was triturated with dichloromethane. The solids were filtered and washed with dichloromethane to give the desired compound contaminated with 30% dechlorinated byproduct (1.3 g, 100%). LCMS calculated for C14H13ClFN2O2 (M+H)+: m/z=295.1. found: 295.0.

Workup

  1. customThe mixture was degassed three times
  2. additionA solution of 0.5 M sodium methoxide in methanol (45 mL) was added
  3. filtrationthe mixture was filtered through celite
  4. customThe filtrates were evaporated
  5. customthe residue was triturated with dichloromethane
  6. filtrationThe solids were filtered
  7. washwashed with dichloromethane

Sources & evidence

ORD record
ord-a8aecba26b3d4cb3ae1d26dccdd1052b
Source dataset
uspto-grants-2015_11
Patent number
US09193721B2

Reaction notes

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