Bromine → HCID 90017290, compound

HRID 1055009Notes

Reaction equation

HRID 1055009 reaction equation
[Br:1]Br.[CH3:3][C:4]1[N:9]=[C:8]([NH2:10])[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][CH:5]=1>FC(F)(F)C(O)=O>[Br:1][C:5]1[CH:6]=[C:7]([C:11]([F:14])([F:12])[F:13])[C:8]([NH2:10])=[N:9][C:4]=1[CH3:3]

Participants

4

Reactant 2

HCID 24408BromineHCID 90018297HCID 90018297, compound

Product 1

HCID 90017290HCID 90017290, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Bromine (1.7 g, 548 μl, 10.6 mmol, Eq: 5) was added to 6-methyl-3-(trifluoromethyl)pyridin-2-amine (375 mg, 2.13 mmol, Eq: 1) in trifluoroacetic acid (7 ml). The mixture was stirred for 30 min and then concentrated to an oil. Water (30 ml) and dichloromethane (10 ml) were added. The mixture was alkalized by addition of sodium bicarbonate and extracted with dichloromethane. The combined organic layers were dried over sodium sulfate and concentrated to an oil. The crude product was purified by chromatography (SiO2, ethyl acetate/n-heptane) to give the desired product (450 mg, 82.9%) as a yellow solid. MS: m/z=255.1 (M+H+)

Workup

  1. concentrationconcentrated to an oil
  2. additionWater (30 ml) and dichloromethane (10 ml) were added
  3. additionThe mixture was alkalized by addition of sodium bicarbonate
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. concentrationconcentrated to an oil
  7. customThe crude product was purified by chromatography (SiO2, ethyl acetate/n-heptane)

Sources & evidence

ORD record
ord-4e24e0f5ee1d4c4f95ae198632bf243f
Source dataset
uspto-grants-2016_07
Patent number
US09394311B2

Reaction notes

Loading…