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Dimethylformamide → 3-bromo-5-(2,6-difluorophenyl)-2-{[2-(trimethylsilyl)ethoxy]methyl}-7-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-4-yl)-2H-pyrazolo[4,3-c]isoquinoline

HRID 1256254
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HRID 1256254 반응식
[Br:1][C:2]1[N:3]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([C:15]4[CH:16]=[N:17][NH:18][CH:19]=4)=[CH:10][C:9]=3[C:8]([C:20]3[C:25]([F:26])=[CH:24][CH:23]=[CH:22][C:21]=3[F:27])=[N:7][C:6]=12.CN(C=O)C.C(N(C(C)C)CC)(C)C.[CH3:50][Si:51]([CH3:58])([CH3:57])[CH2:52][CH2:53][O:54][CH2:55]Cl>O>[Br:1][C:2]1[N:3]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[N:4]=[C:5]2[C:14]3[CH:13]=[CH:12][C:11]([C:15]4[CH:16]=[N:17][N:18]([CH2:55][O:54][CH2:53][CH2:52][Si:51]([CH3:58])([CH3:57])[CH3:50])[CH:19]=4)=[CH:10][C:9]=3[C:8]([C:20]3[C:21]([F:27])=[CH:22][CH:23]=[CH:24][C:25]=3[F:26])=[N:7][C:6]=12
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참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 667722013-bromo-5-(2,6-difluorophenyl)-7-(1H-pyrazol-4-yl)-2-{[2-(trimethylsilyl)ethoxy]methyl}-2H-pyrazolo[4,3-c]isoquinoline

생성물 1

HCID 66772073
3-bromo-5-(2,6-difluorophenyl)-2-{[2-(trimethylsilyl)ethoxy]methyl}-7-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-4-yl)-2H-pyrazolo[4,3-c]isoquinoline

시약·촉매·용매 1

HCID 962Water용매

실험 절차

115 mg of 3-bromo-5-(2,6-difluorophenyl)-7-(1H-pyrazol-4-yl)-2-{[2-(trimethylsilyl)ethoxy]methyl}-2H-pyrazolo[4,3-c]isoquinoline are introduced into 2 ml of DMF, 0.26 ml of diisopropylethylamine and 77 μl of 2-(trimethylsilyl)ethoxymethyl chloride. The reaction mixture is stirred at RT for 18 h and then poured into water, extracted with AcOEt, washed with saturated NaCl solution, dried over MgSO4, filtered and concentrated under RP. The product is purified by chromatography on silica gel (20-45 μm), eluting with a mixture of DCM and methanol (98/02 by vol.), to give 116 mg of 3-bromo-5-(2,6-difluorophenyl)-2-{[2-(trimethylsilyl)ethoxy]methyl}-7-(1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrazol-4-yl)-2H-pyrazolo[4,3-c]isoquinoline (yellow powder). 1H NMR: −0.01 (d, J=5.9 Hz, 4 H) 0.82-1.00 (m, 1 H) 3.60 (t, J=7.8 Hz, 1 H) 3.77 (t, 1 H) 5.46 (s, 1 H) 5.92 (s, 1 H) 7.42 (t, 1 H) 7.71-7.83 (m, 1 H) 8.03 (s, 1 H) 8.28 (dd, 1 H) 8.43 (s, 1 H) 8.58 (d, J=8.3 Hz, 1 H).

후처리

  1. extractionextracted with AcOEt
  2. washwashed with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under RP
  6. customThe product is purified by chromatography on silica gel (20-45 μm)
  7. washeluting with a mixture of DCM and methanol (98/02 by vol.)

출처 및 근거

ORD 기록
ord-0ab19500ba944c74b37d3e76dc5423af
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08461175B2

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