Diethyl Ether → Methyl 2-(5-bromopyridin-3-yl)acetate

HRID 546845Notes

Reaction equation

HRID 546845 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.CCOCC.[Br:13][C:14]1[CH:15]=[C:16]([CH2:20][C:21]([OH:23])=[O:22])[CH:17]=[N:18][CH:19]=1>C1(C)C=CC=CC=1.CO>[CH3:1][O:22][C:21](=[O:23])[CH2:20][C:16]1[CH:17]=[N:18][CH:19]=[C:14]([Br:13])[CH:15]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 28025392-(5-Bromopyridin-3-yl)acetic acid

Product 1

HCID 23398394Methyl 2-(5-bromopyridin-3-yl)acetateYield 72%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

A 2.0 M solution of trimethylsilyldiazomethane in ether (10.3 mL, 20.5 mmol) was added dropwise to a mixed solution of (5-bromo-pyridin-3-yl)-acetic acid (4.04 g, 18.7 mmol) in toluene (17.3 mL) and methanol (11.5 mL), and the mixture was stirred at room temperature for 10 minutes. The reaction solution was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=1:3) to give the title compound (3.12 g, 72%).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=1:3)

Sources & evidence

ORD record
ord-34f6ef86fec74b95b23bb008ce4f0528
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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