HCID 11615162, compound → HCID 86628457, compound

HRID 341609Notes

Reaction equation

HRID 341609 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH2:8][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:18]([CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]1[OH:26])#[CH:19]>>[F:14][C:13]([F:16])([F:15])[C:12]([NH:11][CH2:10][CH2:9][CH2:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:19]#[C:18][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]2[OH:26])[CH:3]=1)=[O:17]

Participants

3

Reactant 2

HCID 11615162HCID 11615162, compoundHCID 57608389N-(3-(3-bromophenyl)propyl)-2,2,2-trifluoroacetamide

Product 1

HCID 86628457HCID 86628457, compound

Procedure

Sonogashira coupling of bromide 3 with 2-ethynylcyclohexanol followed by flash chromatography (5-50% EtOAc/hexanes gradient), gave 2,2,2-trifluoro-N-(3-(3-((2-hydroxycyclohexyl)ethynyl)phenyl)propyl)acetamide as a yellow oil. Yield (1.2 g, 43%): 1H NMR (400 MHz, CDCl3) δ 7.18-7.28 (m, 3H), 7.06-7.30 (m, 3H), 6.33 (brs, 1H), 3.48-3.57 (m, 1H), 3.36 (app q, J=6.8 Hz, 2H), 2.63 (t, J=7.2 Hz, 2H), 2.38-2.46 (m, 1H), 2.32 (brs, 1H), 2.02-2.10 (m, 2H), 1.91 (quint, J=7.2 Hz, 2H), 1.74-1.82 (m, 1H), 1.66-1.74 (m, 1H), 1.40-1.52 (m, 1H), 1.16-1.40 (m, 4H).

Sources & evidence

ORD record
ord-b55a9f69aa6746c98f21cca720404cfe
Source dataset
uspto-grants-2014_11
Patent number
US08895782B2

Reaction notes

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