2-Bromobenzonitrile → 2-{4-[3-(3,5-Difluorophenyl)prop-2-yn-1-yl]piperidin-1-yl}benzonitrile

HRID 1896001Notes

Reaction equation

HRID 1896001 reaction equation
CC1C=CC=C(C#CC=C2CCN(C3C=CC=CC=3)CC2)N=1.[F:23][C:24]1[CH:25]=[C:26]([C:31]#[C:32][CH2:33][CH:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[CH:27]=[C:28]([F:30])[CH:29]=1.Br[C:41]1[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=1[C:43]#[N:44]>>[F:23][C:24]1[CH:25]=[C:26]([C:31]#[C:32][CH2:33][CH:34]2[CH2:35][CH2:36][N:37]([C:41]3[CH:48]=[CH:47][CH:46]=[CH:45][C:42]=3[C:43]#[N:44])[CH2:38][CH2:39]2)[CH:27]=[C:28]([F:30])[CH:29]=1

Participants

4

Reactant 3

HCID 162722-BromobenzonitrileHCID 251838262-Methyl-6-[3-(1-phenylpiperidin-4-ylidene)prop-1-ynyl]pyridineHCID 689794914-[3-(3,5-Difluorophenyl)prop-2-ynyl]piperidine

Product 1

HCID 687237672-{4-[3-(3,5-Difluorophenyl)prop-2-yn-1-yl]piperidin-1-yl}benzonitrile

Procedure

The title compound was prepared following the procedure described for the compound of Example 42, but using Compound 248a instead of the Compound of Example 3 and 2-bromobenzonitrile instead of bromobenzene. The crude was purified by preparative RP LC-MS chromatography, using MS-C18 XTerra column 30×50 mm eluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient, affording the title product as a brown oil.

Workup

  1. customThe title compound was prepared
  2. customThe crude was purified by preparative RP LC-MS chromatography
  3. washeluting with ammonium bicarbonate 20 mM pH 8 buffer-acetonitrile gradient

Sources & evidence

ORD record
ord-cd286be701e8456f9a839329b4d9077e
Source dataset
uspto-grants-2013_08
Patent number
US08518916B2

Reaction notes

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