HCID 131724878, compound → 1H-Indazole

HRID 2181542Notes

Reaction equation

HRID 2181542 reaction equation
C[Si](C)(C)CCOCN1C2C=CC=CC=2N=C1[C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][N:17]=1>O1CCOCC1.CCOC(C)=O>[NH:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:16]=[N:17]1

Participants

4

Reactant 1

HCID 131724878HCID 131724878, compound

Product 1

HCID 92211H-Indazole

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Preparation of 6-[5-methoxy-2-hydroxymethyl-4-(2-trimethylsilanyl-ethoxymethoxy)phenyl]-1-(2-trimethylsilanyl)-ethoxymethyl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1H-indazole: 6-Iodo-1-[2-(trimethyl-silanyl)-ethoxymethyl]-3-{1-[2-(trimethyl-silanyl-ethoxymethyl]-1H-benzoimidazol-2-yl}-1H-indazole [Example 24(a), step (v)] (300 mg, 0.48 mmol) and [4-methoxy-5-(2-trimethylsilanyl)-ethoxymethoxy-2-trimethylstannanyl-phenyl]-methanol (282 mg, 0.63 mmol) were stirred in dioxane (8 mL) under argon at 98° C. for 16 h. The reaction was allowed to cool and was diluted with EtOAc. Organics were washed with sat NaHCO3 and brine, dried (Na2SO4), and concentrated in vacuo. Purification by silica gel chromatography (20% EtOAc/hexanes) gave 224 mg (60%) of 6-[5-methoxy-2-hydroxymethyl(2-trimethylsilanyl-ethoxymethoxy)-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-3-[1-(2-trimethylsilanyl)-ethoxymethyl)-1H-benzoimidazol-2-yl]-1H-indazol as a faint yellow oil. 1H NMR (300 MHz, CDCl3) δ 8.70 (d, 1H, J=8.4 Hz), 7.89-7.92 (m, 1H), 7.63-7.66 (m, 2H), 7.34-7.41 (m, 4H), 6.91 (s, 1H), 6.29 (s, 2H), 5.83 (s, 2H), 5.36 (s, 2H), 4.55 (s, 2H), 3.78-3.92 (m, 5H), 3.59-3.70 (m, 4H), 0.83-1.04 (m, 6H), 0.03 (s, 9H); 40.04 (s, 9H), −0.13 (s, 9 Hz).

Workup

  1. temperatureto cool
  2. washOrganics were washed with sat NaHCO3 and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-a83952aa05684d8f9db9205d53499af2
Source dataset
uspto-grants-2005_05
Patent number
US06891044B2

Reaction notes

Loading…