3-Pentanamine → 5-Chloro-4-iodo-3-(pentan-3-ylamino)picolinonitrile

HRID 2262687Notes

Reaction equation

HRID 2262687 reaction equation
[Cl:1][C:2]1[C:3]([I:11])=[C:4](F)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[NH2:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15]>>[Cl:1][C:2]1[C:3]([I:11])=[C:4]([NH:12][CH:13]([CH2:16][CH3:17])[CH2:14][CH3:15])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 120193-PentanamineHCID 595945425-Chloro-3-fluoro-4-iodopicolinonitrile

Product 1

HCID 595945725-Chloro-4-iodo-3-(pentan-3-ylamino)picolinonitrileYield 100%

Procedure

A solution of 5-chloro-3-fluoro-4-iodopicolinonitrile (46 mg, 0.16 mmol) in 3-aminopentane (1 mL) was heated to 80° C. for 1 h. The reaction mixture was allowed to cool to room temperature, concentrated in vacuo, and then diluted with EtOAc and water. The organic layer was washed with water and filtered through a silica gel plug to provide the title compound as a white powder (55 mg, 100%). m/z=350.1 [M+H]+ and 1H NMR.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with EtOAc and water
  3. washThe organic layer was washed with water
  4. filtrationfiltered through a silica gel plug

Sources & evidence

ORD record
ord-f71916f0974f48a18bc68c1cbe37d36d
Source dataset
uspto-grants-2010_12
Patent number
US07851484B2

Reaction notes

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