Potassium Carbonate → HCID 86650545, compound

HRID 2066649Notes

Reaction equation

HRID 2066649 reaction equation
[Cl:1][C:2]1[N:3]([CH2:10][CH2:11][CH:12]2[CH2:14][O:13]2)[CH:4]=[C:5]([N+:7]([O-:9])=[O:8])[N:6]=1.[Br:15][C:16]1[N:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC.O>[Br:15][C:16]1[N:21]=[CH:20][C:19]([O:22][CH2:14][CH:12]([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:18][CH:17]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27628652-Bromo-5-hydroxypyridineHCID 86650544HCID 86650544, compound

Product 1

HCID 86650545HCID 86650545, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
83.5 °C

Procedure

A mixture of epoxide 129 (see Example 2AA) (1.004 g, 4.61 mmol), 6-bromo-3-pyridinol (4.015 g, 23.1 mmol) and powdered K2CO3 (3.319 g, 24.0 mmol) in anhydrous 2-butanone (10 mL) under N2 was stirred at 82-85° C. for 28 h. The resulting cooled mixture was diluted with water (100 mL) and extracted with 25% EtOAc/CH2Cl2 (3×100 mL). The extracts were evaporated to dryness and the residue was chromatographed on silica gel. Elution with 0-40% EtOAc/petroleum ether firstly gave foreruns, and then further elution with 40% EtOAc/petroleum ether gave 1-[(6-bromo-3-pyridinyl)oxy]-4-(2-chloro-4-nitro-1H-imidazol-1-yl)-2-butanol (137) (667 mg, 37%) as a cream solid: mp (MeOH/CH2Cl2/pentane) 112-114° C.; 1H NMR [(CD3)2SO] δ 8.56 (s, 1H), 8.12 (d, J=3.1 Hz, 1H), 7.53 (d, J=8.8 Hz, 1H), 7.39 (dd, J=8.8, 3.2 Hz, 1H), 5.28 (br d, J=4.5 Hz, 1H), 4.24 (dd, J=14.0, 5.8 Hz, 1H), 4.18 (dd, J=14.2, 7.3 Hz, 1H), 3.99 (dd, J=10.0, 4.9 Hz, 1H), 3.96 (dd, J=10.0, 5.5 Hz, 1H), 3.82 (m, 1H), 2.06 (dtd, J=13.9, 7.7, 3.4 Hz, 1H), 1.90 (ddt, J=13.7, 9.2, 6.7 Hz, 1H); HRESIMS calcd for C12H13BrClN4O4 m/z [M+H]+ 394.9754, 392.9782, 390.9803. found 394.9753, 392.9777, 390.9797.

Workup

  1. temperatureThe resulting cooled mixture
  2. extractionextracted with 25% EtOAc/CH2Cl2 (3×100 mL)
  3. customThe extracts were evaporated to dryness
  4. customthe residue was chromatographed on silica gel
  5. washElution with 0-40% EtOAc/petroleum ether firstly gave foreruns
  6. washfurther elution with 40% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-1ea7402f1d0a4de991e686e210a62203
Source dataset
uspto-grants-2012_10
Patent number
US08293734B2

Reaction notes

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