Ammonium Chloride → N-[2-(4-Biphenyl-4-ylethynyl-phenyl)-1-methyl-ethyl]acetamide

HRID 76198

반응식

HRID 76198 반응식
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]#[C:8][C:9](O)=O)=[CH:3][CH:2]=1.BrC1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([NH:28][C:29](=[O:31])[CH3:30])[CH3:27])=[CH:21][CH:20]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].[NH4+].[Cl-]>CN1C(=O)CCC1>[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([C:7]#[C:8][C:9]2[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([NH:28][C:29](=[O:31])[CH3:30])[CH3:27])=[CH:21][CH:20]=2)=[CH:3][CH:2]=1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 45824256N-(1-(4-bromophenyl)propan-2-yl)acetamideHCID 654541843-([1,1'-Biphenyl]-4-YL)propiolic acid

생성물 1

HCID 66613920N-[2-(4-Biphenyl-4-ylethynyl-phenyl)-1-methyl-ethyl]acetamide

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
90 °C

실험 절차

To 0.22 g (1.00 mmol) biphenyl-4-yl-propynoic acid (I28) and 0.26 g (1.00 mmol) N-[2-(4-bromo-phenyl)-1-methyl-ethyl]-acetamide (I44.1) in 3.00 mL NMP are added 0.06 g (0.10 mmol) 1,1′-bis(diphenylphosphonino)ferrocene, 1.68 g (6.00 mmol) TBAF*H2O and 0.05 g (0.05 mmol) tris(dibenzylidenacetone)dipalladium(0). The reaction mixture is stirred at 90° C. for 3 h. The mixture is allowed to cool to r.t. and poured onto saturated aq NH4Cl solution. The precipitate is filtered, washed with water and purified by column chromatographie (silica gel; DCM/MeOH 9/1). The resulting product is triturated with isopropanol and dried at 60° C. in vacuo.

후처리

  1. temperatureto cool to r.t.
  2. filtrationThe precipitate is filtered
  3. washwashed with water
  4. custompurified by column chromatographie (silica gel; DCM/MeOH 9/1)
  5. customThe resulting product is triturated with isopropanol
  6. customdried at 60° C. in vacuo

출처 및 근거

ORD 기록
ord-d1b2ac7f010d41f2a552465ef9b4c2b2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835472B2

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