3-(Trifluoromethyl)phenylboronic acid → HCID 59318023, compound

HRID 2190673Notes

Reaction equation

HRID 2190673 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:28])[NH:19][C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[C:22](I)[CH:21]=3)=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[F:29][C:30]([F:41])([F:40])[C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1.C(OC(C1CCN(C2C=CC=CN=2)CC1)=O)C>>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:28])[NH:19][C:20]3[CH:21]=[C:22]([C:35]4[CH:34]=[CH:33][CH:32]=[C:31]([C:30]([F:41])([F:40])[F:29])[CH:36]=4)[C:23]([CH3:26])=[CH:24][CH:25]=3)=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 38156184-Piperidinecarboxylic acid, 1-(2-pyridinyl)-, ethyl esterHCID 593180575'-(3-iodo-4-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2]bipyridinyl-4 carboxylic acid ethyl ester

Product 1

HCID 59318023HCID 59318023, compound

Procedure

5′-(6-Methyl-3′-trifluoromethyl-biphenyl-3-ylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]-bipyridinyl-4-carboxylic acid ethyl ester was prepared from 5′-(3-iodo-4-methyl-phenylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4 carboxylic acid ethyl ester and 3-trifluoromethylphenyl boronic acid following a method similar to the one described in the synthesis of 5′42-methyl-biphenyl-4-ylcarbamoyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester above. The product was isolated after silica gel column purification with 20-40% EtOAc in hexanes gradient, HRMS m/z calcd for C28H28N3O3F3 [M+H]+: 512.2156. Found: 512.2155.

Workup

  1. customThe product was isolated
  2. customafter silica gel column purification with 20-40% EtOAc in hexanes gradient, HRMS m/z calcd for C28H28N3O3F3 [M+H]+

Sources & evidence

ORD record
ord-a1914b7c5de946c499f4965ec1db2898
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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