2,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamide → HCID 86635869, compound

HRID 2098535Notes

Reaction equation

HRID 2098535 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][CH:15]=1)[CH2:5][S:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[F:16][C:17]([F:25])([F:24])[C:18]([NH:20][CH2:21][C:22]#[CH:23])=[O:19]>>[CH:7]1([S:6][CH2:5][C:4]2[CH:3]=[C:2]([C:23]#[C:22][CH2:21][NH:20][C:18](=[O:19])[C:17]([F:25])([F:24])[F:16])[CH:15]=[CH:14][CH:13]=2)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

3

Reactant 2

HCID 110948052,2,2-trifluoro-N-(prop-2-yn-1-yl)acetamideHCID 55028052HCID 55028052, compound

Product 1

HCID 86635869HCID 86635869, compound

Procedure

Sonogashira coupling between (3-bromobenzyl)(cyclohexyl)sulfane and 2,2,2-trifluoro-N-(prop-2-ynyl)acetamide following the method used in Example 139 gave N-(3-(3-(cyclohexylthiomethyl)phenyl)prop-2-ynyl)-2,2,2-trifluoroacetamide as a yellow oil. Yield (0.70 g, 35%); 1H NMR (400 MHz, DMSO-d6) δ 10.0 (br t, 1H), 7.24-7.37 (m, 4H), 4.25 (d, J=5.5 Hz, 2H), 3.72 (s, 2H), 2.48-2.53 (m, 1H), 1.79-1.87 (m, 2H), 1.58-1.65 (m, 2H), 1.45-1.52 (m, 1H), 1.12-1.27 (m, 5H).

Sources & evidence

ORD record
ord-e6775fa9b18b4f8dae51de4dce0d2813
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

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