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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
ノート
印刷プレビュー

反応式

HRID 1256254 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

HCID 667720733-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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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.)

出典と根拠

ORDレコード
ord-0ab19500ba944c74b37d3e76dc5423af
出典データセット
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08461175B2

反応ノート

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