Water → Methyl 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate

HRID 1521604Notes

Reaction equation

HRID 1521604 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][C:5]1[CH:6]=[N:7][CH:8]=[C:9]([Br:11])[CH:10]=1.[H-].[Na+].Br[CH2:16][CH2:17]Br.O>CN(C)C=O.O1CCCC1>[Br:11][C:9]1[CH:10]=[C:5]([C:4]2([C:3]([O:2][CH3:1])=[O:12])[CH2:17][CH2:16]2)[CH:6]=[N:7][CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 23398394Methyl 2-(5-bromopyridin-3-yl)acetate

Product 1

HCID 59578399Methyl 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the title compound from Example 71 Step A (0.50 g, 2.17 mmol) in N,N-dimethylformamide (6.8 mL) and tetrahydrofuran (6.8 mL) was added sodium hydride (60% dispersion in mineral oil, 0.435 g, 10.9 mmol). After stirring for 15 minutes, 1,2-dibromoethane (0.56 ml, 6.5 mmol) was added. After stirring overnight, the reaction was poured into water and extracted with ethyl acetate. The combined organic extracts were washed with water and saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated. Purification by flash chromatography on silica gel (20-80% ethyl acetate in hexanes) provided the title compound: LCMS m/z 257.78 [M+2+H]+; 1H NMR (500 MHz, CD3OD) δ 8.53 (s, 1H), 8.49 (s, 1H), 8.02 (s, 1H), 3.63 (s, 3H), 1.64 (m, 2H), 1.29 (m, 2H).

Workup

  1. stirringAfter stirring overnight
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with water and saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by flash chromatography on silica gel (20-80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e0564d22c8434facb90bde59bf3e1b5e
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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