Triethylamine → 2-Chloro-6-[(2,2-dimethyl-propyl)-methyl-amino]-5-fluoro-nicotinonitrile

HRID 852017Notes

Reaction equation

HRID 852017 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([F:10])=[C:4](Cl)[N:3]=1.Cl.[CH3:13][NH:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]([N:14]([CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH3:13])[C:5]([F:10])=[CH:6][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrileHCID 22393520(2,2-Dimethylpropyl)(methyl)amine hydrochloride

Product 1

HCID 865887972-Chloro-6-[(2,2-dimethyl-propyl)-methyl-amino]-5-fluoro-nicotinonitrileYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 2,6-dichloro-3-cyano-5-fluoropyridine (1.0 g, 5.23 mmol), N-methyl-neopentylamine hydrochloride (830 mg, 6.0 mmol) and triethylamine (1.6 mL) in acetonitrile (20 mL) was stirred at room temp for 4 hours. Then volatiles were removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was dried (sodium sulfate) and concentrated in vacuo to afford the product (1.11 g, 83%). C12H15ClFN3 MS m/e=256 (M+H).

Workup

  1. customThen volatiles were removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bee4a51634a74247a55de4f64c83e5c1
Source dataset
uspto-grants-2007_08
Patent number
US07253174B2

Reaction notes

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