2-Bromo-5-hydroxypyridine → HCID 86650548, compound

HRID 2066658Notes

Reaction equation

HRID 2066658 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][C:12]2([CH3:15])[CH2:14][O:13]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[Br:16][C:17]1[N:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1>>[Br:16][C:17]1[N:22]=[CH:21][C:20]([O:23][CH2:14][C:12]([CH3:15])([OH:13])[CH2:11][CH2:10][N:3]2[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=[C:2]2[Cl:1])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 27628652-Bromo-5-hydroxypyridineHCID 86650547HCID 86650547, compound

Product 1

HCID 86650548HCID 86650548, compoundYield 70%

Procedure

Reaction of epoxide 140 (see Example 2JJ) with 6-bromo-3-pyridinol as in Example 2AA at 84° C. for 18.5 h, followed by chromatography of the product on silica gel, eluting with 25-40% EtOAc/petroleum ether (foreruns) and then with 40-50% EtOAc/petroleum ether, gave 1-[(6-bromo-3-pyridinyl)oxy]-4-(2-chloro-4-nitro-1H-imidazol-1-yl)-2-methyl-2-butanol (151) (70%) as a pale yellow-brown foam; 1H NMR (CDCl3) δ 8.09 (dd, J=3.0, 0.3 Hz, 1H), 7.80 (s, 1H), 7.41 (dd, J=8.7, 0.4 Hz, 1H), 7.13 (dd, J=8.7, 3.2 Hz, 1H), 4.29 (ddd, J=14.2, 9.4, 6.4 Hz, 1H), 4.25 (ddd, J=14.1, 9.4, 6.7 Hz, 1H), 3.89 (d, J=8.9 Hz, 1H), 3.86 (d, J=9.0 Hz, 1H), 2.22 (ddd, J=13.9, 9.3, 6.5 Hz, 1H), 2.18 (s, 1H), 2.04 (ddd, J=13.8, 9.4, 6.7 Hz, 1H), 1.42 (s, 3H); HRESIMS calcd for C13H15BrClN4O4 m/z [M+H]+ 408.9910, 406.9939, 404.9960. found 408.9920, 406.9945, 404.9966.

Workup

  1. customat 84° C.
  2. customfor 18.5 h
  3. washeluting with 25-40% EtOAc/petroleum ether (foreruns)

Sources & evidence

ORD record
ord-7077239507524fbaab9dec50f2ab21af
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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