4-Ethynylheptan-4-ol → Tert-butyl 3-fluoro-3-(3-(3-hydroxy-3-propylhex-1-ynyl)phenyl)propylcarbamate

HRID 1021152Notes

Reaction equation

HRID 1021152 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:8]([F:19])[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[CH:6][CH:7]=1.[C:20]([C:22]([OH:29])([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])#[CH:21]>>[F:19][CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([C:21]#[C:20][C:22]([OH:29])([CH2:26][CH2:27][CH3:28])[CH2:23][CH2:24][CH3:25])[CH:3]=1)[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

3

Reactant 2

HCID 123838984-Ethynylheptan-4-olHCID 66743475Tert-butyl 3-(3-bromophenyl)-3-fluoropropylcarbamate

Product 1

HCID 66743011Tert-butyl 3-fluoro-3-(3-(3-hydroxy-3-propylhex-1-ynyl)phenyl)propylcarbamate

Procedure

Sonogashira coupling of tert-butyl 3-(3-bromophenyl)-3-fluoropropylcarbamate and 4-ethynylheptan-4-ol following the method described in Example 12 gives tert-butyl 3-fluoro-3-(3-(3-hydroxy-3-propylhex-1-ynyl)phenyl)propylcarbamate.

Sources & evidence

ORD record
ord-97db041a6d2845b593dbe488a8fb2cb9
Source dataset
uspto-grants-2014_05
Patent number
US08716529B2

Reaction notes

Loading…