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

HRID 405236ノート

反応式

HRID 405236 の反応式
Br[C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1)[CH3:10].CC1(C)C(C)(C)OB([C:33]2[CH:34]=[CH:35][C:36]([C:39]([NH:41][CH2:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])=[O:40])=[N:37][CH:38]=2)O1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.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:8][C:6]1[CH:5]=[CH:4][C:3]([CH:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=3)=[CH:14][CH:13]=2)[CH3:10])=[C:2]([C:33]2[CH:34]=[CH:35][C:36]([C:39]([NH:41][CH2:42][CH2:43][C:44]([O:46][CH2:47][CH3:48])=[O:45])=[O:40])=[N:37][CH:38]=2)[CH:7]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 71059832Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoateHCID 71060075N-(1-(2-bromo-4-chlorophenyl)ethyl)-4'-fluoro-[1,1'-biphenyl]-4-amine

生成物 1

HCID 71060007Ethyl 3-(5-(5-chloro-2-(1-((4'-fluoro-[1,1'-biphenyl]-4-yl)amino)ethyl)phenyl)picolinamido)propanoate

試薬・触媒・溶媒 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 6228Dimethylformamide溶媒

実験手順

N-(1-(2-bromo-4-chlorophenyl)ethyl)-4′-fluoro-[1,1′-biphenyl]-4-amine (138 mg, 0.34 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (142 mg, 0.41 mmol), Pd(dppf)Cl2 (37 mg, 0.05 mmol), and K2CO3 (108 g, 0.78 mmol) were dissolved in wet DMF (3 mL) and water (4 mL) and heated to 90° C. After 16 h the resulting mixture was cooled to room temperature, filtered through CELITE and the filtrate was diluted with EtOAc, washed with water and sat. aqueous NaHCO3. The organic layer was dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

後処理

  1. filtrationfiltered through CELITE
  2. additionthe filtrate was diluted with EtOAc
  3. washwashed with water and sat. aqueous NaHCO3
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified via column chromatography

出典と根拠

ORDレコード
ord-2acd82919088448981d50d61705f75cd
出典データセット
uspto-grants-2014_06
特許番号
US08748624B2

反応ノート

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