Water → HCID 71060009, compound

HRID 405145

Reaction equation

HRID 405145 reaction equation
Br[C:2]1[CH:23]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:21]=[CH:20][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[Cl:19])=[CH:8][CH:7]=1.CC1(C)C(C)(C)OB([C:36]2[CH:37]=[CH:38][C:39]([C:42]([NH:44][CH2:45][CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])=[O:43])=[N:40][CH:41]=2)O1.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:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[C:9]1[CH:10]=[CH:11][C:6]([NH:5][CH2:4][C:3]2[CH:20]=[CH:21][C:22]([C:24]([F:27])([F:26])[F:25])=[CH:23][C:2]=2[C:36]2[CH:37]=[CH:38][C:39]([C:42]([NH:44][CH2:45][CH2:46][C:47]([O:49][CH2:50][CH3:51])=[O:48])=[O:43])=[N:40][CH:41]=2)=[CH:7][CH:8]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 71059832Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoateHCID 86674248N-(2-bromo-4-(trifluoromethyl)benzyl)-2',4'-dichloro-[1,1'-biphenyl]-4-amine

Product 1

HCID 71060009HCID 71060009, compound

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-[1,1′-biphenyl]-4-amine (386 mg, 0.8 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate, prepared as in step a, (424 mg, 1.2 mmol), Pd(dppf)Cl2 (67 mg, 0.1 mmol), and K2CO3 (225 mg, 1.6 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-05d027eacce74e70839d2ea5be5f8ec1
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Linked notes

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