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Ethyl Acetate → 2-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-3-vinyl-1H-indole

HRID 2234077
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HRID 2234077 반응식
I[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]=1[C:11]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)[N:14]=[N:13][C:12]=1[O:23][CH3:24].[CH2:25]([Sn](CCCC)(CCCC)C=C)[CH2:26]CC.[F-].[K+].CCOC(C)=O>[Cl-].C([N+](CC)(CC)CC)C.CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:24][O:23][C:12]1[N:13]=[N:14][C:15]([C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:16][C:11]=1[C:3]1[NH:4][C:5]2[C:10]([C:2]=1[CH:25]=[CH2:26])=[CH:9][CH:8]=[CH:7][CH:6]=2
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 8857Ethyl AcetateHCID 81998TributylvinyltinHCID 522689Potassium FluorideHCID 231029143-Iodo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole

생성물 1

HCID 230925092-(3-Methoxy-6-pyridin-4-yl-pyridazin-4-yl)-3-vinyl-1H-indole

시약·촉매·용매 3

HCID 5946
Tetraethylammonium Chloride
촉매
HCID 178418476HCID 178418476, 화합물촉매
HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A mixture of 430 mg 3-Iodo-2-(3-methoxy-6-pyridin-4-yl-pyridazin-4-yl)-1H-indole, 490 mg tributyl(vinyl)tin, 165 mg tetraethylammonium-chloride and 35 mg bis(triphenylphosphine)palladium(II) chloride in DMF is stirred at 80° C. for 40 min. After cooling to room temperature, 15 ml aqueous potassium fluoride solution (30%) are added and the mixture stirred for 30 min at room temperature before extraction with EtOAc. The organic layer is dried over MgSO4 and the solvent evaporated ion prior to purification of the crude product by preparative RP-HPLC eluting with a gradient of 0-100% acetonitrile in water (+0.01% HCOOH).

후처리

  1. temperatureAfter cooling to room temperature
  2. dry with materialThe organic layer is dried over MgSO4
  3. customthe solvent evaporated ion
  4. customto purification of the crude product by preparative RP-HPLC
  5. washeluting with a gradient of 0-100% acetonitrile in water (+0.01% HCOOH)

출처 및 근거

ORD 기록
ord-61e7c4e3c5674bd895217371c6e2f765
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07709466B2

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