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

HRID 852022Notes

Reaction equation

HRID 852022 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.[CH2:12]([NH2:17])[C:13]([CH3:16])([CH3:15])[CH3:14].C(N(CC)CC)C>C(#N)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:17][CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:5]([F:10])=[CH:6][C:7]=1[C:8]#[N:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79882NeopentylamineHCID 27338492,6-Dichloro-5-fluoro-3-pyridinecarbonitrile

Product 1

HCID 865887982-Chloro-6-[(2,2-dimethyl-propyl)-amino]-5-fluoro-nicotinonitrileYield 87.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,6-dichloro-3-cyano-5-fluoropyridine (1.0 g, 5.23 mmol), neopentylamine (530 mg, 6.0 mmol) and triethylamine (1 mL) in acetonitrile (20 mL) was stirred at room temp for 4 h. After the solvent was removed under reduced pressure, the residue was partitioned between ethyl acetate and water. The organic layer was dried (sodium sulfate) and concentrated under reduced pressure to afford the product (1.11 g, 87%). C11H13ClFN3 MS m/e=242 (M+H).

Workup

  1. customAfter the solvent was removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a9bc7b19f57042fb89de3c888a3a4e03
Source dataset
uspto-grants-2007_08
Patent number
US07253174B2

Reaction notes

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