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3,6-Dichloropyridazine → 3-Chloro-6-(thiophen-2-yl)pyridazine

HRID 1611866
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인쇄 미리보기

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HRID 1611866 반응식
C([Sn]([C:14]1[S:15][CH:16]=[CH:17][CH:18]=1)(CCCC)CCCC)CCC.[Cl:19][C:20]1[N:21]=[N:22][C:23](Cl)=[CH:24][CH:25]=1>CN(C=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:15]1[CH:16]=[CH:17][CH:18]=[C:14]1[C:23]1[N:22]=[N:21][C:20]([Cl:19])=[CH:25][CH:24]=1
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참가 물질

5

반응물 2

HCID 673313,6-DichloropyridazineHCID 27793732-(Tri-n-butylstannyl)thiophene

생성물 1

HCID 64047013-Chloro-6-(thiophen-2-yl)pyridazine수율 47.3%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A mixture of tri-n-butylstannylthiophene (6.26 g, 16.78 mmol), 3,6-dichloropyridazine (5.00 g, 33.56 mmol), tetrakis(triphenylphosphine)palladium(0) (0.20 g, 0.17 mmol) and few crystals of 1,2-ditert-butyl of 2,6-di-tert-butyl-4-methylphenolo in dry DMF (50 mL) was deareated twice with nitrogen. The reaction mixture was heated at 80° C. for 6 hours and, after cooling, poured onto water (100 mL). A white precipitate was collected, washed several times with water and dried under vacuum. This solid was taken up with ether (25 mL) and filtered to afford 3.01 g of almost pure product. Finally, this solid was crystallized from MeOH—H2O to give the pure target compound as white crystals (1.56 g, 7.90 mmol, 47.3% yield). Mp 155° C.; 1H NMR (CDCl3) δ 7.75 (1H, d, 2J=11.0), 7.68 (1H, d, 2J=3.6), 7.54 (1H, d, 2J=5.0), 7.51 (1H, d), 7.18 (1H, dd).

후처리

  1. temperatureafter cooling
  2. additionpoured onto water (100 mL)
  3. customA white precipitate was collected
  4. washwashed several times with water
  5. customdried under vacuum
  6. filtrationfiltered
  7. customto afford 3.01 g of almost pure product
  8. customFinally, this solid was crystallized from MeOH—H2O

출처 및 근거

ORD 기록
ord-d69bbdbfcac440aa8b0000126b909b09
출처 데이터셋
uspto-grants-2006_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06991749B2

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