2-Amino-5-bromo-3-hydroxypyridine → HCID 67463521, compound

HRID 1406273Notes

Reaction equation

HRID 1406273 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([OH:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:12]=1[CH:18](O)[CH3:19]>>[Br:1][C:2]1[CH:3]=[C:4]([O:9][CH:18]([C:12]2[CH:13]=[C:14]([F:17])[CH:15]=[CH:16][C:11]=2[Cl:10])[CH3:19])[C:5]([NH2:8])=[N:6][CH:7]=1

Participants

3

Reactant 2

HCID 116940412-Amino-5-bromo-3-hydroxypyridineHCID 67465447HCID 67465447, compound

Product 1

HCID 67463521HCID 67463521, compound

Procedure

The title compound was prepared by a similar method to that of preparation 18 using commercially available 5-bromo-3-hydroxy-2-amino-pyridine and 1-(2-chloro-5-fluoro-phenyl)-ethanol (prepared according to WO 2009087305 A1) except the reaction time was 18 hr and the crude reaction was purified by chromatography on silica gel eluting initially with ethyl acetate in dichloromethane (2:98) followed by a second purification on silica gel eluting with tert-butyl methyl ether in heptane (45:55) to give a white solid (3.82 g, 49%).

Workup

  1. customthe crude reaction
  2. customwas purified by chromatography on silica gel eluting initially with ethyl acetate in dichloromethane (2:98)
  3. customfollowed by a second purification on silica gel eluting with tert-butyl methyl ether in heptane (45:55)

Sources & evidence

ORD record
ord-656762e4f9e44807b9455cf69c006263
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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