Oxindole → (E)-3-((3-(4-((dimethylamino)methyl)styryl)-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-indazol-6-yl)methylene)indolin-2-one

HRID 1615323

反応式

HRID 1615323 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[CH3:11][N:12]([CH2:14][C:15]1[CH:41]=[CH:40][C:18](/[CH:19]=[CH:20]/[C:21]2[C:29]3[C:24](=[CH:25][C:26]([CH:30]=O)=[CH:27][CH:28]=3)[N:23]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[N:22]=2)=[CH:17][CH:16]=1)[CH3:13]>>[CH3:11][N:12]([CH2:14][C:15]1[CH:16]=[CH:17][C:18]([CH:19]=[CH:20][C:21]2[C:29]3[C:24](=[CH:25][C:26](/[CH:30]=[C:3]4/[C:2](=[O:10])[NH:1][C:9]5[C:4]/4=[CH:5][CH:6]=[CH:7][CH:8]=5)=[CH:27][CH:28]=3)[N:23]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:38])([CH3:39])[CH3:37])[N:22]=2)=[CH:40][CH:41]=1)[CH3:13]

参加物

3

反応物 2

HCID 321710OxindoleHCID 71819503(E)-3-(4-((dimethylamino)methyl)styryl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde

生成物 1

HCID 69812424(E)-3-((3-(4-((dimethylamino)methyl)styryl)-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-indazol-6-yl)methylene)indolin-2-one

実験手順

Synthesized according to the method of Example A19, utilizing indolin-2-one (10.4 mg, 0.0.78 mmol) and (E)-3-(4-((dimethylamino)methyl)styryl)-1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-indazole-6-carbaldehyde (33.4 mg, 0.077 mmol). The crude mixture was concentrated under reduced pressure and purified by prepTLC (SiO2 10% MeOH/DCM) to provide the title compound to as a 1.5-2.0:1.0 (E:Z) mixture of isomers: a yellow solid (29.1 mg, 67%): 1H NMR (400 MHz, CD3OD) δ ppm 9.09-9.14 (s, 0.31H), 8.22 (d, J=8.28 Hz, 0.84H), 8.09 (d, J=8.53 Hz, 0.34H), 7.83-7.87 (m, 1.25H), 7.61-7.69 (m, 4.02H), 7.56-7.60 (m, 1.69H), 7.50 (s, 0.61H), 7.36-7.48 (m, 3.85H), 7.24 (t, J=7.78 Hz, 1.48H), 7.03 (t, J=7.28 Hz, 0.48H), 6.92 (d, J=7.53 Hz, 1.01H), 6.81-6.89 (m, 1.49H), 5.80 (s, 0.60H), 5.78 (s, 1.52H), 3.59-3.65 (m, 2.20H), 2.37-2.42 (m, 7.40H), 0.89 (t, J=8.28 Hz, 3.05H), −0.09 (s, 9H); MS ESI 551.4 [M+H]+, calcd for [C33H38N4O2Si+H]+ 551.8.

後処理

  1. customSynthesized
  2. concentrationThe crude mixture was concentrated under reduced pressure
  3. custompurified by prepTLC (SiO2 10% MeOH/DCM)

出典と根拠

ORDレコード
ord-a5c1a3886e0b4ccfa5dd50c31352c0a4
出典データセット
uspto-grants-2014_07
特許番号
US08765748B2

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