Potassium Carbonate → (E)-3-[3-chloro-4-({5-[(3-fluoro-4-methylbenzyl)oxy]pyridin-2-yl}oxy)-5-methylphenyl]-1-(4-{4-[2-(4-chlorophenoxy)ethyl]benzyl}piperazin-1-yl)prop-2-en-1-one

HRID 1023371노트

반응식

HRID 1023371 반응식
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:17]=[CH:18]/[C:19]([N:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][O:36][C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=4)=[CH:30][CH:29]=3)[CH2:23][CH2:22]2)=[O:20])[CH:5]=[C:6]([CH3:16])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][N:10]=1.[F:44][C:45]1[CH:46]=[C:47]([CH:50]=[CH:51][C:52]=1[CH3:53])[CH2:48]Br.C([O-])([O-])=O.[K+].[K+]>O>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:17]=[CH:18]/[C:19]([N:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([CH2:34][CH2:35][O:36][C:37]4[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=4)=[CH:30][CH:29]=3)[CH2:23][CH2:22]2)=[O:20])[CH:5]=[C:6]([CH3:16])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:48][C:47]2[CH:50]=[CH:51][C:52]([CH3:53])=[C:45]([F:44])[CH:46]=2)=[CH:11][N:10]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 27746033-Fluoro-4-methylbenzyl bromideHCID 67327212(E)-3-{3-chloro-4-[(5-hydroxypyridin-2-yl)oxy]-5-methyl-phenyl}-1-(4-{4-[2-(4-chlorophenoxy)ethyl]benzyl}piperazin-1-yl)prop-2-en-1-one

생성물 1

HCID 53361033(E)-3-[3-chloro-4-({5-[(3-fluoro-4-methylbenzyl)oxy]pyridin-2-yl}oxy)-5-methylphenyl]-1-(4-{4-[2-(4-chlorophenoxy)ethyl]benzyl}piperazin-1-yl)prop-2-en-1-one

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a solution of (E)-3-{3-chloro-4-[(5-hydroxypyridin-2-yl)oxy]-5-methyl-phenyl}-1-(4-{4-[2-(4-chlorophenoxy)ethyl]benzyl}piperazin-1-yl)prop-2-en-1-one (400 mg) was added 3-fluoro-4-methylbenzyl bromide (144 mg) and K2CO3 (134 mg) at room temperature, then the reaction mixture was stirred for 4 hours. The reaction mixture was diluted with H2O and extracted with AcOEt. The organic layer was washed with water and saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt) to afford (E)-3-[3-chloro-4-({5-[(3-fluoro-4-methylbenzyl)oxy]pyridin-2-yl}oxy)-5-methylphenyl]-1-(4-{4-[2-(4-chlorophenoxy)ethyl]benzyl}piperazin-1-yl)prop-2-en-1-one as a colorless amorphous (430 mg).

후처리

  1. extractionextracted with AcOEt
  2. washThe organic layer was washed with water and saturated aqueous NaCl
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (AcOEt)

출처 및 근거

ORD 기록
ord-60268068e5234e4086e3145a1c770635
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722663B2

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