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

HRID 1615319Notes

Reaction equation

HRID 1615319 reaction equation
C1N(P(N2CC2)(NC(C2C(I)=CC=CC=2)=O)=O)C1.[CH3:19][N:20]1[CH:24]=[CH:23][N:22]=[C:21]1[CH:25]=[CH2:26].I[C:28]1[C:36]2[C:31](=[CH:32][C:33]([CH:37]=[O:38])=[CH:34][CH:35]=2)[N:30]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[N:29]=1>>[CH3:19][N:20]1[CH:24]=[CH:23][N:22]=[C:21]1/[CH:25]=[CH:26]/[C:28]1[C:36]2[C:31](=[CH:32][C:33]([CH:37]=[O:38])=[CH:34][CH:35]=2)[N:30]([CH2:39][O:40][CH2:41][CH2:42][Si:43]([CH3:46])([CH3:45])[CH3:44])[N:29]=1

Participants

4

Reactant 3

HCID 197801IodobenzotefHCID 5722461-Methyl-2-vinyl-1H-imidazoleHCID 581896963-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde

Product 1

HCID 86651978(E)-3-(2-(1-methyl-1H-imidazol-2-yl)vinyl)-1-((2-(trimethylsilyl)-ethoxy)methyl)-1H-indazole-6-carbaldehydeYield 17%

Procedure

The title compound was synthesized according to the method of Example A103, utilizing 1-methyl-2-vinyl-1H-imidazole (35 mg, 0.32 mmol) and 3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole-6-carbaldehyde (100 mg, 0.23 mmol). Purified by prepTLC (SiO2 10% MeOH/DCM) to provide the title compound (15 mg, 74%) as a tan oil (41.6 mg, 47%). 1H NMR (400 MHz, CD3OD) δ ppm 10.09 (s, 1H), 8.22 (t, J=1.00 Hz, 1H), 8.13 (d, J=8.53 Hz, 1H), 7.78 (dd, J=8.53, 1.25 Hz, 1H), 7.68 (d, J=16.06 Hz, 1H), 7.43 (d, J=16.06 Hz, 1H), 7.13 (d, J=1.25 Hz, 1H), 7.05 (d, J=1.00 Hz, 1H), 5.84 (s, 2H), 4.89 9s, 3H), 3.63 (t, J=8.03 Hz, 1H), 0.87 (t, J=8.03 Hz, 2H), −0.10 (s, 9H); MS ESI 383.2 [M+H]+, calcd for [C20H26N4O2Si+H]+ 383.5.

Workup

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

Sources & evidence

ORD record
ord-e9ecd3f9f1354d519398b875a7c4a29c
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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