[2-(3-Methoxypropyl)phenyl]boronic acid → 3-{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[2'-(3-methoxypropyl)-3-(trifluoromethyl)biphenyl-4-yl]propanenitrile

HRID 2194902Notes

Reaction equation

HRID 2194902 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][O:21][C:22]3[C:27]([Cl:28])=[CH:26][C:25]([CH3:29])=[CH:24][C:23]=3[Cl:30])=[CH:14][CH:13]=2)[C:9]#[N:10])=[C:4]([C:31]([F:34])([F:33])[F:32])[CH:3]=1.[CH3:35][O:36][CH2:37][CH2:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1B(O)O>>[Cl:30][C:23]1[CH:24]=[C:25]([CH3:29])[CH:26]=[C:27]([Cl:28])[C:22]=1[O:21][CH2:20][CH2:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][CH:8]([C:5]2[CH:6]=[CH:7][C:2]([C:45]3[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=3[CH2:39][CH2:38][CH2:37][O:36][CH3:35])=[CH:3][C:4]=2[C:31]([F:34])([F:33])[F:32])[C:9]#[N:10])=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 58083347[2-(3-Methoxypropyl)phenyl]boronic acidHCID 866588532-[4-Bromo-2-(trifluoromethyl)phenyl]-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propanenitrile

Product 1

HCID 674474133-{4-[2-(2,6-Dichloro-4-methylphenoxy)ethoxy]phenyl}-2-[2'-(3-methoxypropyl)-3-(trifluoromethyl)biphenyl-4-yl]propanenitrile

Procedure

Prepared according to the procedure described in EXAMPLE 7, step 2 using 2-[4-bromo-2-(trifluoromethyl)phenyl]-3-{4-[2-(2,6-dichloro-4-methylphenoxy)ethoxy]phenyl}propanenitrile from step 1 and [2-(3-methoxypropyl)phenyl]boronic acid from EXAMPLE 3, step 1 as starting materials. Purification by column chromatography on silica gel (Combi-Flash by ISCO), eluting with Hex/EtOAc (5 to 10%, in 30 min) afforded the desired compound as a colorless oil.

Workup

  1. customPrepared
  2. customPurification by column chromatography on silica gel (Combi-Flash by ISCO)
  3. washeluting with Hex/EtOAc (5 to 10%, in 30 min)

Sources & evidence

ORD record
ord-1f82e39967824ca4b7c46d17c57e4593
Source dataset
uspto-grants-2012_12
Patent number
US08334308B2

Reaction notes

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