783339-45-7 → HCID 86635864, compound

HRID 2098519Notes

Reaction equation

HRID 2098519 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.[C:19]([CH:21]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)#[CH:20]>>[CH:21]1([C:19]#[C:20][C:2]2[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]=2)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

3

Reactant 2

HCID 21600274783339-45-7HCID 57608426N-(3-(3-bromophenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide

Product 1

HCID 86635864HCID 86635864, compound

Procedure

Sonogashira coupling of N-(3-(3-bromophenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide (43) with ethynylcycloheptane, followed by flash chromatography (5-40% EtOAc/hexanes gradient), gave N-(3-(3-(cycloheptylethynyl)phenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide as an amber oil. Yield (0.507 g, 51%): 1H NMR (400 MHz, CDCl3) δ 7.42 (br s, 1H), 7.34-7.36 (m, 1H), 7.19-7.33 (m, 3H), 4.81 (q, J=4.0 Hz, 1H), 3.48-3.68 (m, 1H), 3.32-3.42 (m, 1H), 2.74-2.82 (m, 1H), 2.48 (br s, 1H), 1.85-2.00 (m, 4H), 1.70-1.80 (m, 4H), 2.46-1.64 (m, 6H).

Sources & evidence

ORD record
ord-1bce11b3e86d4cff9c31e3bf3f0979a5
Source dataset
uspto-grants-2013_05
Patent number
US08450527B2

Reaction notes

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