Diisopropylethylamine → HCID 58980644, compound

HRID 735803Notes

Reaction equation

HRID 735803 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[N:8]=[C:7]([Br:15])[C:6]=1[OH:16])[CH3:2].[CH:18](N(CC)C(C)C)(C)C.C[Si](C=[N+]=[N-])(C)C>C(#N)C.CO>[CH2:1]([O:3][C:4](=[O:17])[C:5]1[CH:10]=[C:9]([C:11]([CH3:12])([CH3:13])[CH3:14])[N:8]=[C:7]([Br:15])[C:6]=1[O:16][CH3:18])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 58980648Ethyl 2-bromo-6-(1,1-dimethylethyl)-3-hydroxy-4-pyridinecarboxylate

Product 1

HCID 58980644HCID 58980644, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 21959252Acetonitrile methanolSolvent

Procedure

To a solution of the above bromopyridine (2.74 g, 9.07 mmol) in acetonitrile/methanol (9:1, 33 mL) was added N,N-diisopropylethylamine (2.50 mL, 14.2 mmol) followed by (trimethylsilyl)diazomethane (2.0M in hexane, 7.0 mL, 14.2 mmol). The red solution was stirred 0.5 h at room temperature then concentrated in vacuo. The residue was dissolved in methylene chloride, washed with saturated aqueous NaHCO3, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 2-bromo-6-tert-butyl-3-methoxy-isonicotinic acid ethyl ester (2.65 g, 93%) as a red oil which was utilized without further purification.

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in methylene chloride
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3959b4ecab84203864e32467d187703
Source dataset
uspto-grants-2009_09
Patent number
US07592332B2

Reaction notes

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