N-bromobutanimide → 3-(Benzyloxy)-5-bromopyridin-2-amine

HRID 1766715Notes

Reaction equation

HRID 1766715 reaction equation
[NH2:1][C:2]1[C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[Br:16]N1C(=O)CCC1=O>CC#N.CCOC(C)=O>[CH2:9]([O:8][C:7]1[C:2]([NH2:1])=[N:3][CH:4]=[C:5]([Br:16])[CH:6]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 903342-Amino-3-benzyloxypyridine

Product 1

HCID 206265543-(Benzyloxy)-5-bromopyridin-2-amineYield 53%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-amino-3-benzyloxypyridine (42.0 g, 0.21 mol) in CH3CN (600 mL) at 0° C. was added N-bromosuccinimide (37.1 g, 0.21 mol) over 30 minutes. The mixture was stirred for 0.5 hr, after which the reaction was then diluted with EtOAc (900 mL) and partitioned with H2O (900 mL). The organic layer was washed with brine and dried (Na2SO4), filtered and concentrated to dryness under vacuum to yield 3-benzyloxy-5-bromo-pyridin-2-ylamine (31.0 g, 0.11 mol, 53%). 1H NMR (CDCl3, 300 MHz) δ 4.63–4.78 (brs, 2H), 5.04 (s, 2H), 7.07 (d, 1H, J, 1.8 Hz), 7.33–7.42 (m, 5H), 7.73 (d, 1H, J, 1.8 Hz).

Workup

  1. custompartitioned with H2O (900 mL)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under vacuum

Sources & evidence

ORD record
ord-e51e516695574c39890ecf188000bf8c
Source dataset
uspto-grants-2007_06
Patent number
US07230098B2

Reaction notes

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