Hydrochloric Acid → 5-Bromo-2-chloro-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridine

HRID 1497765Notes

Reaction equation

N(OC(C)(C)C)=O.[Br:8][C:9]1[C:10]([CH3:26])=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[C:12](N)=[N:13][CH:14]=1.[ClH:27]>CC#N.[Cu](Cl)Cl>[Br:8][C:9]1[C:10]([CH3:26])=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=2)[C:12]([Cl:27])=[N:13][CH:14]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a suspension of copper (II) chloride (421 mg, 3.92 mmol) and t-butyl nitrite (466 μL, 3.92 mmol) in dry MeCN (12 mL) at 70° C. was added 5-bromo-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridin-2-ylamine (Int. 1, 864 mg, 2.61 mmol) dropwise as a solution in MeCN (3 mL) over 5 mins. The reaction mixture was stirred at 70° C. for 3.5 hrs then poured onto 5 N aqueous HCl (20 mL). The reaction mixture was extracted with EtOAc (4×20 mL) then the combined organic extracts were dried (Na2SO4), filtered and evaporated in vacuo. The resultant residue was purified by flash chromatography, eluting with a gradient of 0-100% EtOAc in cyclohexane to give the title compound as an orange solid (184 mg).

Workup

extractionThe reaction mixture was extracted with EtOAc (4×20 mL)
dry with materialthe combined organic extracts were dried (Na2SO4)
filtrationfiltered
customevaporated in vacuo
customThe resultant residue was purified by flash chromatography
washeluting with a gradient of 0-100% EtOAc in cyclohexane

Sources & evidence

ORD record: ord-887b71d5c8e14694b4b2af04e5e9801e
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199984B2

Reaction notes

Loading…