Iodobenzotef → (E)-3-(4-((dimethylamino)methyl)styryl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde

HRID 1615322

반응식

HRID 1615322 반응식
C1N(P(N2CC2)(NC(C2C(I)=CC=CC=2)=O)=O)C1.[CH3:19][N:20]([CH3:30])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH:28]=[CH2:29])=[CH:24][CH:23]=1.I[C:32]1[C:40]2[C:35](=[CH:36][C:37]([CH:41]=[O:42])=[CH:38][CH:39]=2)[N:34]([CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[N:33]=1>>[CH3:19][N:20]([CH2:21][C:22]1[CH:27]=[CH:26][C:25](/[CH:28]=[CH:29]/[C:32]2[C:40]3[C:35](=[CH:36][C:37]([CH:41]=[O:42])=[CH:38][CH:39]=3)[N:34]([CH2:43][O:44][CH2:45][CH2:46][Si:47]([CH3:50])([CH3:49])[CH3:48])[N:33]=2)=[CH:24][CH:23]=1)[CH3:30]

참가 물질

4

반응물 3

HCID 197801IodobenzotefHCID 519956Benzenemethanamine, ar-ethenyl-N,N-dimethyl-HCID 581896963-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde

생성물 1

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

실험 절차

The title compound was synthesized according to the method of Example A103, utilizing N,N-dimethyl-1-(4-vinylphenyl)methanamine (42 mg, 0.26 mmol) and 3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (70 mg, 0.17 mmol). Purified by prepTLC (SiO2 10% MeOH/DCM) to provide the title compound to as a pale orange gum (33.4 mg, 44%). 1H NMR (400 MHz, CD3OD) δ ppm 10.13 (s, 1H), 8.27 (m, 2H), 7.81 (d, J=9.29 Hz, 1H), 7.69 (d, J=8.28 Hz, 2H), 7.61 (d, J=16.6 Hz, 1H), 7.50 (d, J=16.6 Hz, 1H), 7.43 (d, J=8.28 Hz, 2H), 5.86 (s, 2H), 3.82 (s, 2H), 3.62 (t, J=8.03 Hz, 1H), 2.50 (s, 6H), 0.87 (t, J=8.03 Hz, 2H), −0.09 (s, 9H); MS ESI 436.3 [M+H]+, calcd for [C25H33N3O2Si+H]+ 436.6.

후처리

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

출처 및 근거

ORD 기록
ord-ffbb96f1b6334ea1bc77ef415b69abd2
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08765748B2

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