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

HRID 1615324Notes

Reaction equation

HRID 1615324 reaction equation
C1N(P(N2CC2)(NC(C2C(I)=CC=CC=2)=O)=O)C1.[CH:19]([C:21]1[CH:22]=[C:23]([C:27]([N:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[O:28])[CH:24]=[CH:25][CH:26]=1)=[CH2:20].I[C:37]1[C:45]2[C:40](=[CH:41][C:42]([CH:46]=[O:47])=[CH:43][CH:44]=2)[N:39]([CH2:48][O:49][CH2:50][CH2:51][Si:52]([CH3:55])([CH3:54])[CH3:53])[N:38]=1>>[CH3:35][N:32]1[CH2:31][CH2:30][N:29]([C:27]([C:23]2[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=2)/[CH:19]=[CH:20]/[C:37]2[C:45]3[C:40](=[CH:41][C:42]([CH:46]=[O:47])=[CH:43][CH:44]=3)[N:39]([CH2:48][O:49][CH2:50][CH2:51][Si:52]([CH3:55])([CH3:54])[CH3:53])[N:38]=2)=[O:28])[CH2:34][CH2:33]1

Participants

4

Reactant 3

HCID 197801IodobenzotefHCID 581896963-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehydeHCID 687307791-[(3-Ethenylphenyl)carbonyl]-4-methylpiperazine

Product 1

HCID 86651981(E)-3-(3-(4-methylpiperazine-1-carbonyl)styryl)-1-((2-(trimethylsilyl)ethoxy)-methyl)-1H-indazole-6-carbaldehyde

Procedure

The title compound was synthesized according to the method of Example A103, utilizing 1-[(3-ethenylphenyl)carbonyl]-4-methylpiperazine (76 mg, 0.33 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 colorless material (30.1 mg, 24%). 1H NMR (400 MHz, CD3OD) δ ppm 10.14 (s, 1H), 8.27 (s, 1H), 7.80 (m, 1H), 7.71 (s, 1H), 7.65 (d, J=16.6 Hz, 1H), 7.56-7.60 (m, 1H), 7.57 (s, 1H), 7.48-7.55 (m, 2H), 7.35 (d, J=7.28 Hz, 1H), 5.86 (s, 2H), 3.69-3.90 (m, 2H), 3.63 (t, J=7.91 Hz, 2H), 3.43-3.56 (m, 2H), 2.40-2.64 (m, 4H), 2.35 (s, 3H), 0.88 (t, J=7.91 Hz, 2H), −0.09 (m, 9H); MS ESI 505.4 [M+H]+, calcd for [C28H36N4O3Si+H]+ 505.7.

Workup

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

Sources & evidence

ORD record
ord-3686ac9208e842588b16eee61def3053
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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