Sodium Carbonate → HCID 67021267, 화합물

HRID 1660972노트

반응식

HRID 1660972 반응식
[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]

참가 물질

10

반응물 4

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

생성물 1

HCID 67021267HCID 67021267, 화합물

시약·촉매·용매 5

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 702Ethanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 21863594Toluene ethanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-219dc7064d8642329f035cb0067ebc95
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030311B2

반응 노트

불러오는 중…