2-Methylpyrrolidine → 5-Methyl-6-(2-methylpyrrolidin-1-yl)nicotinonitrile

HRID 400753Notes

Reaction equation

HRID 400753 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH3:10])[C:6](F)=[N:7][CH:8]=1)#[N:2].[CH3:11][CH:12]1[CH2:16][CH2:15][CH2:14][NH:13]1.CCN(C(C)C)C(C)C>C(O)CCC>[CH3:10][C:5]1[C:6]([N:13]2[CH2:14][CH2:15][CH2:16][CH:12]2[CH3:11])=[N:7][CH:8]=[C:3]([CH:4]=1)[C:1]#[N:2]

Participants

5

Reactant 3

HCID 130032-MethylpyrrolidineHCID 81531DiisopropylethylamineHCID 232882695-Cyano-2-fluoro-3-picoline

Product 1

HCID 673978125-Methyl-6-(2-methylpyrrolidin-1-yl)nicotinonitrileYield 101.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 5-cyano-2-fluoro-3-methylpyridine (Molekula, 400 mg; 2.94 mmol) in 1-butanol (1 mL), 2-methylpyrrolidine (Acros, 300 mg; 3.53 mmol) and DIEA (1.52 mL; 8.82 mmol) was heated at 90° C. for 18 hours. Reaction mixture was partitioned between EtOAc and water and washed with water to give the title compound as a yellow oil (600 mg, quantitative). HPLC (Method A) Rt 1.99 min (Purity: 96.1%). LC/MS (Method B): 202.1 (M+H)+.

Workup

  1. customReaction mixture
  2. customwas partitioned between EtOAc and water
  3. washwashed with water

Sources & evidence

ORD record
ord-783753dcc80e497c8f2cf27653f51c32
Source dataset
uspto-grants-2014_06
Patent number
US08741923B2

Reaction notes

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