(tert-Butyldimethylsilyl)acetylene → 5-Bromo-2-[(tert-butyldimethylsilanyl)ethynyl]-3-fluoropyridine

HRID 734890Notes

Reaction equation

HRID 734890 reaction equation
Br[C:2]1[C:7]([F:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[C:10]([Si:14]([C:17]#[CH:18])([CH3:16])[CH3:15])([CH3:13])([CH3:12])[CH3:11]>>[Br:9][C:5]1[CH:6]=[C:7]([F:8])[C:2]([C:18]#[C:17][Si:14]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:16])[CH3:15])=[N:3][CH:4]=1

Participants

3

Reactant 2

HCID 2757281(tert-Butyldimethylsilyl)acetyleneHCID 224128322,5-Dibromo-3-fluoropyridine

Product 1

HCID 690610065-Bromo-2-[(tert-butyldimethylsilanyl)ethynyl]-3-fluoropyridine

Procedure

The product was prepared analogously to Example 48.1c from 23.4 g (92.0 mmol) of 2,5-dibromo-3-fluoropyridine and 17.5 mL (92.0 mmol) of tert-butylethynyldimethylsilane (with triethylamine as base and PdCl2(PPh3)2 as catalyst). Yield: 23.3 g (81% of theoretical); C13H17BrFNSi (M=314.269); calc.: molpeak (M+H)+:314/316 (Br); found: molpeak (M+H)+:314/316 (Br).

Sources & evidence

ORD record
ord-e2267c8d0bd34b59952a6f475fca47d8
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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