Water → Ethyl 3-(5-(2-(((4'-chloro-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405163

反応式

HRID 405163 の反応式
Br[C:2]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][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][CH:13]=2)=[CH:8][CH:7]=1.CC1(C)C(C)(C)OB([C:35]2[CH:36]=[CH:37][C:38]([C:41]([NH:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])=[O:42])=[N:39][CH:40]=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:18][C:15]1[CH:16]=[CH:17][C:12]([C:9]2[CH:10]=[CH:11][C:6]([NH:5][CH2:4][C:3]3[CH:19]=[CH:20][C:21]([C:23]([F:26])([F:25])[F:24])=[CH:22][C:2]=3[C:35]3[CH:36]=[CH:37][C:38]([C:41]([NH:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])=[O:42])=[N:39][CH:40]=3)=[CH:7][CH:8]=2)=[CH:13][CH:14]=1

参加物

8

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 71059832Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoateHCID 71059841N-(2-bromo-4-(trifluoromethyl)benzyl)-4'-chloro-[1,1'-biphenyl]-4-amine

生成物 1

HCID 71060037Ethyl 3-(5-(2-(((4'-chloro-[1,1'-biphenyl]-4-yl)amino)methyl)-5-(trifluoromethyl)phenyl)picolinamido)propanoate

試薬・触媒・溶媒 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

N-(2-bromo-4-(trifluoromethyl)benzyl)-4′-chloro-[1,1′-biphenyl]-4-amine (1.4 g, 3.1 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate, prepared as in step a, (1.6 g, 4.7 mmol), Pd(dppf)Cl2 (255 mg, 0.3 mmol), and K2CO3 (859 mg, 6.2 mmol) were dissolved in 1,4-dioxane (24 mL) and water (6 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.

後処理

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

出典と根拠

ORDレコード
ord-50cc0b77398c45cf9ce20691cf3fe815
出典データセット
uspto-grants-2014_06
特許番号
US08748624B2

関連ノート

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