Bromine → 5-(5-Bromo-2-(4-fluorophenyl)oxazol-4-yl)-3-methoxypyridin-2-amine

HRID 538418Notes

Reaction equation

HRID 538418 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[C:11]([C:13]3[CH:14]=[C:15]([O:20][CH3:21])[C:16]([NH2:19])=[N:17][CH:18]=3)[N:12]=2)=[CH:4][CH:3]=1.[Br:22]Br>C(Cl)(Cl)Cl>[Br:22][C:10]1[O:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[N:12][C:11]=1[C:13]1[CH:14]=[C:15]([O:20][CH3:21])[C:16]([NH2:19])=[N:17][CH:18]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 665905395-(2-(4-Fluorophenyl)oxazol-4-yl)-3-methoxypyridin-2-amine

Product 1

HCID 665911705-(5-Bromo-2-(4-fluorophenyl)oxazol-4-yl)-3-methoxypyridin-2-amineYield 74.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 5-(2-(4-fluorophenyl)oxazol-4-yl)-3-methoxypyridin-2-amine (145 mg, 0.5 mmol) in chloroform (20 mL) at 0° C. was added a pre-cooled solution of bromine (40 μL, 0.7 mmol) in CHCl3 (5 mL). The reaction mixture was stirred for <5 min, concentrated in vacuo, and the resulting residue was azeotroped with CHCl3 (2×). Purification by flash chromatography (SiO2, 100:0-95:5 DCM-MeOH) provided 135 mg of 5-(5-bromo-2-(4-fluorophenyl)oxazol-4-yl)-3-methoxypyridin-2-amine as a yellow solid: LCMS (m/z): 365.8 (MH+), tR=0.83 min.

Workup

  1. concentrationconcentrated in vacuo
  2. customthe resulting residue was azeotroped with CHCl3 (2×)
  3. customPurification by flash chromatography (SiO2, 100:0-95:5 DCM-MeOH)

Sources & evidence

ORD record
ord-e1e365f0a20b4ebc8592067a511e63c0
Source dataset
uspto-grants-2014_10
Patent number
US08865732B2

Reaction notes

Loading…