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Stannane, tributyl(1-ethoxyethenyl)- → 6-[6-(1-Ethoxy-vinyl)-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl]-7-fluoro-quinoline

HRID 456166
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HRID 456166 반응식
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][C:21]=3[F:22])[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:28]([O:30][CH2:31][CH3:32])=[CH2:29])CCC>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>[CH2:31]([O:30][C:28]([C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]3[CH:13]=[C:14]4[C:19](=[CH:20][C:21]=3[F:22])[N:18]=[CH:17][CH:16]=[CH:15]4)[N:9]=[N:10][C:5]2=[N:4][CH:3]=1)=[CH2:29])[CH3:32]
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참가 물질

5

반응물 2

HCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 593418366-[(6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl]-7-fluoroquinoline

생성물 1

HCID 581904906-[6-(1-Ethoxy-vinyl)-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl]-7-fluoro-quinoline

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

A mixture of 6-(6-bromo-[1,2,3]triazolo[4,5-b]pyrazin-1-ylmethyl)-7-fluoro-quinoline (2.0 g, 5.57 mmol), Pd(Ph3P)4(0.64 g, 0.56 mmol) and tributyl(1-ethoxyvinyl)stannane (4.02 g, 11.14 mmol) in DMF (50 mL) was flushed with nitrogen and then heated at 100° C., stirred for 7 hours. Removal of the solvent under reduced pressure, the residue was diluted with DCM, washed sequentially with KF (aq.) and water, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by silica gel column chromatography with gradient (DCM:MeOH=50:1) to give the title compound as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ ppm 9.11 (s, 1H), 8.93 (d, 1H), 8.40 (d, 1H), 8.15 (d, 1H), 7.83 (d, 1H), 7.54 (m, 1H), 6.22 (s, 2H), 5.50 (d, 1H), 4.73 (d, 1H), 4.02 (q, 2H), 1.40 (t, 3H). LCMS (method E): [MH]+=351, tR=5.42 min.

후처리

  1. customwas flushed with nitrogen
  2. customRemoval of the solvent under reduced pressure
  3. additionthe residue was diluted with DCM
  4. washwashed sequentially with KF (aq.) and water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel column chromatography with gradient (DCM:MeOH=50:1)

출처 및 근거

ORD 기록
ord-69c41c90679c4721b660d111db64fdf8
출처 데이터셋
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08497368B2

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