Trifluoroacetic acid → 6-Bromo-5-fluoropyridin-2-amine

HRID 1396478Notes

Reaction equation

HRID 1396478 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([Br:15])[N:9]=1)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:15][C:10]1[N:9]=[C:8]([NH2:7])[CH:13]=[CH:12][C:11]=1[F:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71744124Tert-butyl (6-bromo-5-fluoropyridin-2-YL)carbamate

Product 1

HCID 596058336-Bromo-5-fluoropyridin-2-amineYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (6-bromo-5-fluoro-pyridin-2-yl)-carbamic acid tert-butyl ester (1.43 g, 4.91 mmol) in DCM (25 mL) was added TFA (3.78 mL, 49.1 mmol, Eq: 10.0). The mixture was stirred at room temperature for 2 h, after which it was concentrated in vacuo, and redissolved in EtOAc. The organic layer was washed with sat. aq. NaHCO3 followed by water and brine. The resulting organic layer was concentrated on to silica gel and chromatographed (10% to 40% EtOAc/hexanes) to give 6-bromo-5-fluoro-pyridin-2-ylamine (850 mg, 91%). 1H NMR (400 MHz, CHLOROFORM-d6) δ ppm 7.23 (dd, J=8.6, 7.5 Hz, 1H), 6.41 (dd, J=8.6, 2.6 Hz, 1H), 4.40 (br. s, 2H).

Workup

  1. concentrationafter which it was concentrated in vacuo
  2. dissolutionredissolved in EtOAc
  3. washThe organic layer was washed with sat. aq. NaHCO3
  4. concentrationThe resulting organic layer was concentrated on to silica gel
  5. customchromatographed (10% to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-cc36f01cdd014233bd45c2777bbfdcf9
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

Loading…