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Cesium carbonate → Ethyl 5-(5-formylfuran-2-yl)nicotinate

HRID 1645265
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HRID 1645265 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:19]=2)[C:14]([O:16][CH2:17][CH3:18])=[O:15])O1.Br[C:22]1[O:26][C:25]([CH:27]=[O:28])=[CH:24][CH:23]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O.O1CCOCC1.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]>[CH:27]([C:25]1[O:26][C:22]([C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:19]=2)[C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:23][CH:24]=1)=[O:28]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10796Cesium carbonateHCID 6003285-Bromofuran-2-carbaldehydeHCID 3816953Ethyl 5-(tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylate

생성물 1

HCID 59190169Ethyl 5-(5-formylfuran-2-yl)nicotinate수율 100.2%

시약·촉매·용매 3

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 962Water용매
HCID 218864351,4-Dioxane--water (1/1)용매

실험 절차

A solution of ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (570 mg, 2.06 mmol), 5-bromofuran-2-carbaldehyde (300 mg, 1.71 mmol), Cs2CO3 (1.125 g, 3.46 mmol) and PdCl2(dppf) (65 mg, 0.09 mmol) in H2O/dioxane (5%, 10 mL) was heated at reflux for 15 min. The reaction mixture was cooled to rt and diluted with H2O (100 mL). The resulting precipitate was collected by filtration to yield the desired ethyl 5-(5-formylfuran-2-yl)nicotinate (420 mg). LCMS (ES): m/z 246 [M+1]+.

후처리

  1. temperatureat reflux for 15 min
  2. filtrationThe resulting precipitate was collected by filtration

출처 및 근거

ORD 기록
ord-f59a0ff580b74294aa6c0754a5bc9847
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08124649B2

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