Dimethylformamide → 6-pyridin-4-yl-1-(2-trimethylsilanyl-ethoxymethyl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1H-indazole

HRID 724445Notes

Reaction equation

HRID 724445 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:15]=[C:14]3[C:10]([C:11](C=O)=[N:12][N:13]3[CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.C1(N)[C:27]([NH2:32])=[CH:28][CH:29]=[CH:30][CH:31]=1.[S].[CH3:35][N:36]([CH:38]=[O:39])[CH3:37]>[Cl-].[Na+].O>[N:1]1[CH:2]=[CH:3][C:4]([C:7]2[CH:15]=[C:14]3[C:10]([C:11]([C:37]4[N:36]([CH2:38][O:39][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:35]5[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=5[N:32]=4)=[N:12][N:13]3[CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:21])[CH3:22])=[CH:9][CH:8]=2)=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7243O-PhenylenediamineHCID 5362487SulfurHCID 21877293HCID 21877293, compound

Product 1

HCID 218775286-pyridin-4-yl-1-(2-trimethylsilanyl-ethoxymethyl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1H-indazoleYield 65%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of 6-pyridin-4-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole-3-carbaldehyde (0.70 g, 2.0 mmol), benzene-1,2-diamine (0.26 g, 2.4 mmol) and sulfur (77 mg, 2.4 mmol) in DMF (10 ml) was heated in an oil bath at 90° C. overnight. The resulting mixture was poured into brine (200 ml), then extracted with EtOAc (3×60 ml). The combined organic layer was dried over MgSO4 and concentrated under reduced pressure. The resulting oil was purified by silica gel chromatography to yield 6-pyridin-4-yl-1-(2-trimethylsilanyl-ethoxymethyl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1H-indazole as a light brown oil (0.75 g, 65%). 1H NMR (CDCl3) δ 8.82 (d, 1H, J=8.5 Hz), 8.73 (d, 1H, J=5.8 Hz), 7.94–7.89 (m, 2H), 7.87 (s, 1H), 7.69–7.62 (m, 4H), 7.40–7.34 (m, 2H), 3.70–3.49 (m, 4H), 0.94 (t, 2H, J=8.3 Hz), 0.67 (t, 2H, J=8.2 Hz), −0.03 (s, 9H), −0.13 (s, 9H).

Workup

  1. extractionextracted with EtOAc (3×60 ml)
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting oil was purified by silica gel chromatography

Sources & evidence

ORD record
ord-24bd31b3dfca41b4b40abcd07809c058
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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