Sodium Carbonate → HCID 67021267、化合物

HRID 1660972ノート

反応式

HRID 1660972 の反応式
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]3[CH:17]=[CH:18][C:19](Br)=[CH:20][C:15]=3[N:14]=[CH:13]2)=[CH:8][CH:7]=1)[CH3:2].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+].B(O)O>C1(C)C=CC=CC=1.CCO.CCO.CCOC(C)=O.O.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]>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([C:28]4[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=4)=[CH:20][C:15]=3[N:14]=[CH:13]2)=[CH:8][CH:7]=1)[CH3:2]

参加物

10

反応物 4

HCID 10340Sodium CarbonateHCID 61668Boronic AcidHCID 201262(4-Methoxyphenyl)boronic acidHCID 67021635[4-(5-Bromo-benzoimidazol-1-yl)-phenyl]-acetic acid ethyl ester

生成物 1

HCID 67021267HCID 67021267、化合物

試薬・触媒・溶媒 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 702Ethanol溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 21863594Toluene ethanol溶媒

実験手順

A mixture of [4-(5-bromo-benzoimidazol-1-yl)-phenyl]-acetic acid ethyl ester (0.300 g, 0.84 mmol), 4-methoxyphenylboronic acid (0.152 g, 1.00 mmol, 1.2 equiv), PdCl2(dppf) (18 mg, 0.025 mmol, 0.03 equiv), Na2CO3 (2 M solution in H2O, 1.7 mL, 3.34 mmol, 4 equiv) in toluene/EtOH (12 mL; 5:1, v/v) is stirred and refluxed for 2 h. After further addition of boronic acid (0.100 g, 0.66 mmol) in EtOH (1 mL), the reaction mixture is stirred and refluxed for 30 min, allowed to cool to rt, diluted with EtOAc and H2O, and filtered through a pad of Celite. The layers are separated and the aqueous phase is extracted with EtOAc. The combined organic phase is washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Silica gel column chromatography purification (Hexane/EtOAc, 3:1) provides the title compound as a yellow solid: ES-MS: 387.1 [M+H]+; single peak at tR=4.27 min (System 1); Rf=0.24 (Hexane/EtOAc, 3:1).

後処理

  1. temperaturerefluxed for 2 h
  2. stirringthe reaction mixture is stirred
  3. temperaturerefluxed for 30 min
  4. filtrationfiltered through a pad of Celite
  5. customThe layers are separated
  6. extractionthe aqueous phase is extracted with EtOAc
  7. washThe combined organic phase is washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customSilica gel column chromatography purification (Hexane/EtOAc, 3:1)

出典と根拠

ORDレコード
ord-219dc7064d8642329f035cb0067ebc95
出典データセット
uspto-grants-2011_10
特許番号
US08030311B2

反応ノート

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