HCID 15172910, compound → HCID 87082349, compound

HRID 341630Notes

Reaction equation

HRID 341630 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.[CH2:19]([CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[CH2:20][C:21]#[CH:22]>>[CH:23]1([CH2:19][CH2:20][C:21]#[C:22][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]1

Participants

3

Reactant 2

HCID 15172910HCID 15172910, compoundHCID 57608426N-(3-(3-bromophenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide

Product 1

HCID 87082349HCID 87082349, compound

Procedure

Sonogashira reaction of 25 with but-3-ynyl-cyclopentane yielded N-(3-(3-(4-cyclopentylbut-1-ynyl)phenyl)-3-hydroxypropyl)-2,2,2-trifluoroacetamide as a dark brown oil. Yield (690 mg, 69%): 1H NMR (400 MHz, CDCl3) δ 7.22-7.57 (m, 4H), 4.85 (m, 1H), 3.65-3.72 (m, 1H), 3.36-3.45 (m, 1H), 2.41 (t, J=8.0 Hz, 2H), 2.37 (bs, 1H), 1.90-1.97 (m, 3H), 1.80-1.82 (m, 2H), 1.54-1.59 (m, 4H), 1.51-1.53 (m, 2H), 1.12-1.15 (m, 2H).

Sources & evidence

ORD record
ord-cdb346b5cd5a4b14bfe1694254454b51
Source dataset
uspto-grants-2014_11
Patent number
US08895782B2

Reaction notes

Loading…