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

HRID 1666065Notes

Reaction equation

HRID 1666065 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-ab2b7a9638c642ed972175bdad57a4ca
Source dataset
uspto-grants-2011_10
Patent number
US08044040B2

Reaction notes

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