Triethylamine → 2-Chloro-5-fluoropyridine-3-carbonitrile
Reaction equation
[Cl:1][C:2]1[N:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([NH2:6])=O.CCN(CC)CC.C(OC(C(F)(F)F)=O)(C(F)(F)F)=O>C(Cl)Cl>[Cl:1][C:2]1[N:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]#[N:6]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A suspension of crude compound 3 (65 g, 372.4 mmol) and Et3N (114 mL, 819.2 mmol) in DCM (700 mL) was cooled to 0° C. and TFAA (57 mL, 409.6 mmol) was added dropwise. The resulting yellow solution was stirred for 90 minutes at 0° C., diluted with DCM, washed with sat. aq. NaHCO3 and brine, and dried (Na2SO4). The mixture was filtered and concentrated. Kugel Rohr distillation of the residue (˜70° C./1 mbar) gave 50 g (86%) of compound 4 as a beige solid.
Workup
- washwashed with sat. aq. NaHCO3 and brine
- dry with materialdried (Na2SO4)
- filtrationThe mixture was filtered
- concentrationconcentrated
- distillationKugel Rohr distillation of the residue (˜70° C./1 mbar)
Sources & evidence
- ORD record
- ord-bc2fbcf46fcd4704900ba55da77a29ee
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08664219B2
Reaction notes
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