Water → HCID 67281724, compound

HRID 575739Notes

Reaction equation

HRID 575739 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[CH:12]1([CH2:15][OH:16])[CH2:14][CH2:13]1.CC([O-])(C)C.[K+].O>C1COCC1>[Br:1][C:2]1[C:3]([O:16][CH2:15][CH:12]2[CH2:14][CH2:13]2)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 75644CyclopropanemethanolHCID 2308893-Bromo-2-chloro-5-nitropyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 67281724HCID 67281724, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-bromo-2-chloro-5-nitropyridine (2.4 g, 10 mmol) and cyclopropylmethanol (970 uL, 12 mmol) in THF (50 ml) was treated with KOtBu (3.3 g, 15 mmol). After stirring at rt for 12 h, the mixture was treated with water (150 ml) and extracted with EtOAc (3×50 ml); the combined organic extracts were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to afford a yellow solid. The solid was purified by silica gel column chromatography using a gradient of EtOAc (5 to 30%) in hexanes to afford the title compound (1.3 g, 48%) as a yellow solid. LCMS (M+H)+=274.

Workup

  1. extractionextracted with EtOAc (3×50 ml)
  2. washthe combined organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford a yellow solid
  7. customThe solid was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-bd92afd479ae493590faf4b3e854365b
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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