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

HRID 1666060
Notes
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Reaction equation

HRID 1666060 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-b74eb0428b1b4efbbc6f27e3c2ab23a3
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08044040B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes