4-Methoxybut-1-yne → 2,2,2-Trifluoro-n-(3-hydroxy-3-(3-(4-methoxybut-1-ynyl)phenyl)propyl)acetamide

HRID 517134Notes

Reaction equation

HRID 517134 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([OH:18])[CH2:9][CH2:10][NH:11][C:12](=[O:17])[C:13]([F:16])([F:15])[F:14])[CH:5]=[CH:6][CH:7]=1.[CH3:19][O:20][CH2:21][CH2:22][C:23]#[CH:24]>>[F:14][C:13]([F:16])([F:15])[C:12]([NH:11][CH2:10][CH2:9][CH:8]([OH:18])[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:24]#[C:23][CH2:22][CH2:21][O:20][CH3:19])[CH:3]=1)=[O:17]

Participants

3

Reactant 2

HCID 5421524-Methoxybut-1-yneHCID 57608426N-(3-(3-bromophenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide

Product 1

HCID 870824892,2,2-Trifluoro-n-(3-hydroxy-3-(3-(4-methoxybut-1-ynyl)phenyl)propyl)acetamide

Procedure

Sonogashira reaction of 25 with 4-methoxy-but-1-yne yielded 2,2,2-trifluoro-N-(3-hydroxy-3-(3-(4-methoxybut-1-ynyl)phenyl)propyl)acetamide as a dark yellow oil. Yield (0.51 g, 51%). Compound could not be purified completely and was forwarded as such into the next step.

Sources & evidence

ORD record
ord-fb237bfee877492c89c4bbee9e25734b
Source dataset
uspto-grants-2015_08
Patent number
US09115056B2

Reaction notes

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