Hydrochloric Acid → 1-{4-[4-(5-Acetyl-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone

HRID 736191

反応式

HRID 736191 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)=[C:6]([CH:25]=1)[C:7]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][C:16]=2[F:24])[CH2:11][CH2:10]1)=[O:8].C([Sn](CCCC)(CCCC)[C:37]([O:39]CC)=[CH2:38])CCC.Cl>C1(C)C=CC=CC=1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:37]([C:2]1[CH:3]=[CH:4][C:5]([N:26]2[CH2:27][CH2:28][O:29][CH2:30][CH2:31]2)=[C:6]([CH:25]=1)[C:7]([N:9]1[CH2:10][CH2:11][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:23])[CH3:22])=[CH:17][C:16]=2[F:24])[CH2:13][CH2:14]1)=[O:8])(=[O:39])[CH3:38]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 445805131-(4-(4-(5-Bromo-2-morpholinobenzoyl)piperazin-1-yl)-3-fluorophenyl)ethanone

生成物 1

HCID 597935521-{4-[4-(5-Acetyl-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone収率 10%

試薬・触媒・溶媒 2

HCID 178418476HCID 178418476、化合物触媒HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a suspension of 1-{4-[4-(5-Bromo-2-morpholin-4-yl-benzoyl)-piperazin-1-yl]-3-fluoro-phenyl}-ethanone (160 mg, 0.33 mmol) in toluene (2 ml) were added PdCl2(PPh3)2 (5 mg, 0.0065 mmol) and tributyl(1-ethoxyvinyl) tin (125 ul, 0.36 mmol). The mixture was heated to 100° C. for 6 hours. The mixture was cooled in an ice bath and 2N HCl (0.55 ml) was added. The mixture was stirred at room temperature overnight. The mixture was filtered. The organic layer was separated and 10% aqueous KF solution was added. The mixture was stirred at room temperature for 3 hours and filtered. The organic layer was dried over Na2SO4, filtered and the solvent was removed in vacuo. The crude gum was chromatographed on silica gel, eluent: heptane/ethylacetate 0%-50% (10 minutes) to provide the title compound (15 mg, 10%) as a white solid MS (m/e): 454.2 (M+H, 100%).

後処理

  1. temperatureThe mixture was cooled in an ice bath
  2. filtrationThe mixture was filtered
  3. customThe organic layer was separated
  4. addition10% aqueous KF solution was added
  5. stirringThe mixture was stirred at room temperature for 3 hours
  6. filtrationfiltered
  7. dry with materialThe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. customthe solvent was removed in vacuo
  10. customThe crude gum was chromatographed on silica gel, eluent

出典と根拠

ORDレコード
ord-d956c20305fc4f61a652155aeb5955c5
出典データセット
uspto-grants-2009_09
特許番号
US07595314B2

関連ノート

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