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Sodium Carbonate → Ethyl 2-(2-methoxyphenyl)-1,3-thiazole-4-carboxylate

HRID 460186
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HRID 460186 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.Br[C:13]1[S:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:13]1[S:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylateHCID 27339582-Methoxyphenylboronic acid

생성물 1

HCID 10015624Ethyl 2-(2-methoxyphenyl)-1,3-thiazole-4-carboxylate

시약·촉매·용매 2

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매
HCID 8071
1,2-Dimethoxyethane
용매

실험 절차

A suspension of 2-methoxyphenyl boronic acid (0.25 g, 1.65 mmol), ethyl 2-bromothiazole-4-carboxylate (0.33 g, 1.4 mmol), PdCl2(dppf)2 (0.11 g, 0.14 mmol) and 2M Na2CO3(aq) (2 mL) in DME (10 mL) was heated at reflux for 20 h, cooled to RT, filtered, concentrated by rotary evaporation and purified on silica gel (6:1 hexanes/EtOAc and 4:1 hexanes/EtOAc) to afford the title compound as a light-brown oil. EI-MS m/z 264 (M+H).

후처리

  1. temperaturewas heated
  2. temperatureat reflux for 20 h
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. custompurified on silica gel (6:1 hexanes/EtOAc and 4:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-6368c9f9dfd4423097c10d98956241d3
출처 데이터셋
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07196104B2

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