N-bromobutanimide → 5-Bromo-3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine

HRID 1766732Notes

Reaction equation

[Cl:1][C:2]1[C:16]([F:17])=[CH:15][CH:14]=[C:13]([Cl:18])[C:3]=1[CH2:4][O:5][C:6]1[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][CH:11]=1.C1C(=O)N([Br:26])C(=O)C1>C(#N)C>[Br:26][C:10]1[CH:11]=[C:6]([O:5][CH2:4][C:3]2[C:13]([Cl:18])=[CH:14][CH:15]=[C:16]([F:17])[C:2]=2[Cl:1])[C:7]([NH2:12])=[N:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

5-bromo-3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine was prepared following procedure 1. A stirring solution of 3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine (9.07 g, 0.03 mol) in acetonitrile was cooled to 0° C. using an ice bath. To this solution was added NBS (5.33 g, 0.03 mol) portionwise. The reaction was stirred at 0° C. for 15 min. The reaction was concentrated to dryness under vacuum. The resulting dark oil was dissolved in EtOAc (500 mL), and purified via silica gel chromatography. The solvents were then removed in vacuo to yield 5-bromo-3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine (5.8 g, 0.015 mol, 51%) as a white crystaline solid.

Workup

custom5-bromo-3-(2,6-dichloro-3-fluoro-benzyloxy)-pyridin-2-ylamine was prepared
concentrationThe reaction was concentrated to dryness under vacuum
dissolutionThe resulting dark oil was dissolved in EtOAc (500 mL)
custompurified via silica gel chromatography
customThe solvents were then removed in vacuo

Sources & evidence

ORD record: ord-9804539b13084a53843e23ecd0c5ff58
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230098B2

Reaction notes

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