Trifluoroacetic acid methylene chloride → 2-Chloro-3-fluoropyridin-4-amine

HRID 59944Notes

Reaction equation

HRID 59944 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[C:6]([NH:9]C(=O)OC(C)(C)C)[CH:5]=[CH:4][N:3]=1.C(O)(C(F)(F)F)=O.C(Cl)Cl>>[Cl:1][C:2]1[C:7]([F:8])=[C:6]([NH2:9])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86723306Tert-butyl (2-chloro-3-fluoropyridin-4-yl)carbamate

Product 1

HCID 601502892-Chloro-3-fluoropyridin-4-amine

Procedure

A solution of tert-butyl N-(2-chloro-3-fluoro-4-pyridyl)carbamate (20.2 mmol) in 1:2 TFA/DCM (45 mL) was stirred at room temperature for 6 h. The reaction mixture was concentrated and the residue was purified by flash column chromatography (SiO2, 100:0 to 90:10 DCM/7N NH3 in MeOH) to yield the desired product.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by flash column chromatography (SiO2, 100:0 to 90:10 DCM/7N NH3 in MeOH)

Sources & evidence

ORD record
ord-cf5a7b68adc8497681ed4d00ea860847
Source dataset
uspto-grants-2016_09
Patent number
US09440929B2

Reaction notes

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