Citric Acid → HCID 68961151、化合物

HRID 2191821ノート

反応式

HRID 2191821 の反応式
[NH2:1][C:2]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:16]=2)[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:36]1[CH:37]=[CH:38][C:39]2[S:43][CH:42]=[CH:41][C:40]=2[CH:44]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[S:43]1[C:39]2[CH:38]=[CH:37][C:36]([NH:1][C:2]3[CH:14]=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH:16]=4)[CH:12]=[CH:11][C:3]=3[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])=[CH:44][C:40]=2[CH:41]=[CH:42]1

参加物

10

反応物 5

HCID 311Citric AcidHCID 10796Cesium carbonate2 回HCID 27765785-Bromo-1-benzothiophene2 回HCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl3 回HCID 68958545HCID 68958545、化合物

生成物 1

HCID 68961151HCID 68961151、化合物

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒3 回HCID 9811564Bis(dibenzylideneacetone)palladium触媒3 回HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
110 °C

実験手順

To toluene 3.0 mL suspension of tert-butyl 2-amino-4-(3-(tert-butoxycarbonyloxy)phenyl)benzoate 0.12 g and cesium carbonate 0.25 g were added 5-bromobenzothiophene 0.13 g, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 7.4 mg, tris(dibenzylideneacetone)dipalladium(0) 2.9 mg and palladium acetate 1.4 mg at room temperature, and it was stirred at 110° C. for 24 hours. 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 7.4 mg, tris(dibenzylideneacetone)dipalladium(0) 2.9 mg and palladium acetate 1.4 mg were added to it, and it was stirred at 110° C. for 21 hours. Cesium carbonate 51 mg, 5-bromobenzothiophene 33 mg, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl 7.4 mg, tris(dibenzylideneacetone)dipalladium(0) 2.9 mg and palladium acetate 1.4 mg were added to it, and it was stirred at 110° C. for 24 hours. After the reaction mixture was cooled to room temperature, ethyl acetate and 10% citric acid aqueous solution were added to it, and insoluble matter was filtrated. The organic layer was separated and collected,dried over anhydrous magnesium sulfate after washing with saturated sodium chloride aqueous solution, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=10:1] to give tert-butyl 2-((benzothiophen-5-yl)amino)-4-(3-(tert-butoxycarbonyloxy)phenyl)benzoate.

後処理

  1. stirringwas stirred at 110° C. for 21 hours
  2. stirringwas stirred at 110° C. for 24 hours
  3. temperatureAfter the reaction mixture was cooled to room temperature
  4. filtrationwas filtrated
  5. customThe organic layer was separated
  6. washafter washing with saturated sodium chloride aqueous solution
  7. customthe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-8836dc27c4ef411597c74f9ef60d5307
出典データセット
uspto-grants-2012_12
特許番号
US08327467B2

反応ノート

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