Methyl 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate → HCID 66788306, compound

HRID 391326Notes

Reaction equation

HRID 391326 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:11]([O:13]C)=[O:12])[CH2:10][CH2:9]2)[CH:5]=[N:6][CH:7]=1.O([Si](C)(C)C)[K:16]>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2([C:11]([O-:13])=[O:12])[CH2:9][CH2:10]2)[CH:5]=[N:6][CH:7]=1.[K+:16]

Participants

4

Reactant 2

HCID 59578399Methyl 1-(5-bromopyridin-3-yl)cyclopropanecarboxylateHCID 178504318HCID 178504318, compound

Product 1

HCID 66788306HCID 66788306, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate (1 g, 3.9 mmol) in THF (40 mL) was added 90% KOTMS (0.557 g, 3.9 mmol), and the mixture was stirred at room temperature overnight. The mixture was filtered and washed with THF to give potassium 1-(5-bromopyridin-3-yl)cyclopropanecarboxylate. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.63-0.69 (m, 2H), 1.09-1.15 (m, 2H), 7.79-7.80 (m, 1H), 8.34-8.37 (m, 2H).

Workup

  1. filtrationThe mixture was filtered
  2. washwashed with THF

Sources & evidence

ORD record
ord-696bf8c1647b4b37a8c48e4a6c936a7e
Source dataset
uspto-grants-2013_02
Patent number
US08383827B2

Reaction notes

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