Iodobenzotef → (E)-3-(2-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)vinyl)-1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-indazole-6-carbaldehyde

HRID 1615326ノート

反応式

HRID 1615326 の反応式
C1N(P(N2CC2)(NC(C2C(I)=CC=CC=2)=O)=O)C1.[CH3:19][N:20]1[CH2:25][CH2:24][N:23]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]=[CH2:33])=[CH:28][N:27]=2)[CH2:22][CH2:21]1.I[C:35]1[C:43]2[C:38](=[CH:39][C:40]([CH:44]=[O:45])=[CH:41][CH:42]=2)[N:37]([CH2:46][O:47][CH2:48][CH2:49][Si:50]([CH3:53])([CH3:52])[CH3:51])[N:36]=1>>[CH3:19][N:20]1[CH2:21][CH2:22][N:23]([C:26]2[N:27]=[CH:28][C:29](/[CH:32]=[CH:33]/[C:35]3[C:43]4[C:38](=[CH:39][C:40]([CH:44]=[O:45])=[CH:41][CH:42]=4)[N:37]([CH2:46][O:47][CH2:48][CH2:49][Si:50]([CH3:53])([CH3:52])[CH3:51])[N:36]=3)=[CH:30][CH:31]=2)[CH2:24][CH2:25]1

参加物

4

反応物 3

HCID 197801IodobenzotefHCID 581896963-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehydeHCID 667303221-Methyl-4-(5-vinylpyridin-2-yl)piperazine

生成物 1

HCID 71819373(E)-3-(2-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)vinyl)-1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-indazole-6-carbaldehyde

実験手順

The title compound was synthesized according to the method of Example A103, utilizing 1-methyl-4-(5-vinylpyridin-2-yl)piperazine (65 mg, 0.32 mmol) and 3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (100 mg, 0.25 mmol). Purified by prepTLC (SiO2 10% MeOH/DCM) to provide the title compound to as a pale orange material (46 mg, 39%). 1H NMR (400 MHz, CD3OD) δ ppm 10.14 (s, 1H), 8.34 (d, J=2.26 Hz, 1.0H), 8.24-8.28 (m, 2H), 8.00 (dd, J=8.91, 2.38 Hz, 1H), 7.80 (d, J=8.78 Hz, 1H), 7.51 (d, J=16.56 Hz, 1H), 7.36 (d, J=16.56 Hz, 1H), 6.97 (d, J=9.29 Hz, 1H), 5.85 (s, 2H), 3.77-3.87 (m, 4H), 3.63 (t, J=7.91 Hz, 2H), 3.06-3.15 (m, 4H), 2.75 (s, 3H), 0.88 (t, J=8.03 Hz, 2H), −0.09 (s, 9H); MS ESI 478.3 [M+H]+, calcd for [C26H35N5O2Si+H]+ 478.7.

後処理

  1. customThe title compound was synthesized
  2. customPurified by prepTLC (SiO2 10% MeOH/DCM)

出典と根拠

ORDレコード
ord-fe8eaafbe925437b9d6d44eb2e6a26d1
出典データセット
uspto-grants-2014_07
特許番号
US08765748B2

反応ノート

読み込み中…