Trimethylsilylacetylene → 2,2,2-Trifluoro-N-{2-(methyloxy)-5[(trimethylsilyl)ethynyl]phenyl}-acetamide

HRID 1157639Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]([O:15][CH3:16])=[C:6]([NH:8][C:9](=[O:14])[C:10]([F:13])([F:12])[F:11])[CH:7]=1.[CH3:17][Si:18]([C:21]#[CH:22])([CH3:20])[CH3:19]>>[F:11][C:10]([F:13])([F:12])[C:9]([NH:8][C:6]1[CH:7]=[C:2]([C:22]#[C:21][Si:18]([CH3:20])([CH3:19])[CH3:17])[CH:3]=[CH:4][C:5]=1[O:15][CH3:16])=[O:14]

Participants

Reactant 2

HCID 66111Trimethylsilylacetylene

HCID 22636844N-[5-bromo-2-(methyloxy)phenyl]-2,2,2-trifluoroacetamide

Product 1

HCID 595114262,2,2-Trifluoro-N-{2-(methyloxy)-5[(trimethylsilyl)ethynyl]phenyl}-acetamideYield 38%

Procedure

N-[5-Bromo-2-(methyloxy)phenyl]-2,2,2-trifluoroacetamide (5.79 g, 19.4 mmol) and (trimethylsilyl)acetylene (4.1 mL, 29.1 mmol) were coupled according to the procedure of Example 56, Step B to give the desired product (2.32 g, 38%). ES-LC/MS m/z=314 [M−H]−.

Sources & evidence

ORD record: ord-b42daa7aa5524ca6a0242f35f2609900
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07807673B2

Reaction notes

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