3-(1,1-Dimethoxy-methyl)-6-[2-methoxy4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole → 6-[2-methoxy4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole-3-carbaldehyde

HRID 724416Notes

Reaction equation

HRID 724416 reaction equation
C[O:2][CH:3]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([C:15]3[CH:20]=[CH:19][C:18]([O:21][CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])=[CH:17][C:16]=3[O:30][CH3:31])=[CH:12][CH:13]=2)[N:8]([CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])[N:7]=1)OC>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH3:31][O:30][C:16]1[CH:17]=[C:18]([O:21][CH2:22][O:23][CH2:24][CH2:25][Si:26]([CH3:29])([CH3:28])[CH3:27])[CH:19]=[CH:20][C:15]=1[C:11]1[CH:10]=[C:9]2[C:14]([C:6]([CH:3]=[O:2])=[N:7][N:8]2[CH2:32][O:33][CH2:34][CH2:35][Si:36]([CH3:39])([CH3:38])[CH3:37])=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 218774213-(1,1-Dimethoxy-methyl)-6-[2-methoxy4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole

Product 1

HCID 218773756-[2-methoxy4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole-3-carbaldehydeYield 100%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

3-(1,1-Dimethoxy-methyl)-6-[2-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (1.1 g, 1.92 mmol) was stirred in 1% TFA/CH2Cl2 (20 mL) for 1 h at rt. Concentration in vacuo yielded 1.01 g (100%) of 6-[2-methoxy-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole-3-carbaldehyde as a clear oil. 1H NMR (300 MHz, CDCl3) δ 10.27 (s, 1H), 8.28 (d, 1H, J=8.4 Hz), 7.73 (s, 1H), 7.55 (dd, 1H, J=8.4, 1.2 Hz), 7.29 (d, 1H, J=8.4 Hz), 6.72–6.79 (m, 2H), 5.82 (s, 2H), 5.28 (s, 2H), 3.78–3.84 (m, 5H), 3.61 (t, 2H, J=8.1 Hz), 0.89–1.03 (m, 4H), 0.03 (s, 9H), −0.05 (s, 9H).

Workup

  1. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-a599810d4abb4b00a4eaf7bbaf0fb957
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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