Pyridine → HCID 67228918, compound

HRID 1515578Notes

Reaction equation

HRID 1515578 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]#[C:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:7]([NH2:16])=[N:6][CH:5]=1.N1C=CC=CC=1.[C:24](Cl)(=[O:26])[CH3:25]>ClCCl>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([C:10]#[C:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:7]([NH:16][C:24](=[O:26])[CH3:25])=[N:6][CH:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 67228299HCID 67228299, compound

Product 1

HCID 67228918HCID 67228918, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 6-amino-5-trimethylsilanylethynyl-nicotinic acid methyl ester (6.05 g, 24.4 mmol) and pyridine (4 mL, 49.4 mmol) in dichloromethane (80 mL) was added acetyl chloride (2.6 mL, 35.6 mmol) at 0° C. The mixture was allowed to warm up to 25° C. and stirred for 12 h. The reaction mixture was extracted with ethyl acetate, washed with brine and dried over sodium sulfate. The solvent was evaporated in vacuo to afford 6-acetylamino-5-trimethylsilanylethynyl nicotinic acid methyl ester which was used without further purification.

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-413a4cd528984cdda807d7a7a78d840f
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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