Trimethylsilylacetylene → Methyl 5-((trimethylsilyl)ethynyl)nicotinate

HRID 55304

Reaction equation

HRID 55304 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[C:8](Br)[CH:7]=[N:6][CH:5]=1.[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14]>>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[C:8]([C:17]#[C:16][Si:13]([CH3:15])([CH3:14])[CH3:12])[CH:7]=[N:6][CH:5]=1

Participants

3

Reactant 2

HCID 66111TrimethylsilylacetyleneHCID 699336Methyl 5-bromopyridine-3-carboxylate

Product 1

HCID 53821751Methyl 5-((trimethylsilyl)ethynyl)nicotinateYield 13.6%

Procedure

Under the conditions of example 21 B, 5 g of 5-bromonicotinic acid methyl ester is reacted with 2.43 g of trimethylsilylacetylene, worked up, and the crude product is chromatographed on silica gel with hexane/0-5% ethyl acetate. 734 mg of 5-(2-trimethlsilylethinyl)-nicotinic acid methyl ester is obtained as oil.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-5% ethyl acetate

Sources & evidence

ORD record
ord-b32f6a6c03b1401f8f6ebe00916729cb
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Linked notes

Loading…