Water → Methyl 2'-(((2,4'-dichloro-2'-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-2-methyl-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate

HRID 2167135Notes

Reaction equation

HRID 2167135 reaction equation
Br[C:2]1[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:21][C:3]=1[CH2:4][NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[CH3:19])=[C:8]([Cl:20])[CH:7]=1.[CH3:29][C:30]1[CH:31]=[C:32]([CH:37]=[CH:38][C:39]=1B1OC(C)(C)C(C)(C)O1)[C:33]([O:35][CH3:36])=[O:34].C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:20][C:8]1[CH:7]=[C:6]([NH:5][CH2:4][C:3]2[CH:21]=[CH:22][C:23]([C:25]([F:28])([F:27])[F:26])=[CH:24][C:2]=2[C:39]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][C:30]=2[CH3:29])[CH:11]=[CH:10][C:9]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[CH3:19]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 110870242-Methyl-4-methoxycarbonylphenylboronic acid, pinacol esterHCID 86674206N-(2-bromo-4-(trifluoromethyl)benzyl)-2,4'-dichloro-2'-methyl-[1,1'-biphenyl]-4-amine

Product 1

HCID 71060183Methyl 2'-(((2,4'-dichloro-2'-methyl-[1,1'-biphenyl]-4-yl)amino)methyl)-2-methyl-5'-(trifluoromethyl)-[1,1'-biphenyl]-4-carboxylate

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

N-(2-bromo-4-(trifluoromethyl)benzyl)-2,4′-dichloro-2′-methyl-[1,1′-biphenyl]-4-amine, prepared as described in Example 1, (500 mg, 1.0 mmol), methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (339 mg, 1.2 mmol), Pd(dppf)Cl2 (84 mg, 0.1 mmol), and K2CO3 (283 mg, 2.0 mmol) were dissolved in 1,4-dioxane (8 mL) and water (2 mL) and the resulting mixture was heated to 80° C. After 16 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry

Sources & evidence

ORD record
ord-369894951c154bd59ee0707b83d1a640
Source dataset
uspto-grants-2015_06
Patent number
US09045389B2

Reaction notes

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