6-[5-methoxy-2-methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-(2-trimethylsilanyl-ethoxymethyl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1H-indazole → 3-1H-Benzoimidazol-2-yl-6-(2-(hydroxymethyl)-5-methoxy-4-hydroxy-phenyl)-1H-indazole

HRID 724410Notes

Reaction equation

HRID 724410 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:45]COCC[Si](C)(C)C)=[CH:5][C:6]([CH2:43][OH:44])=[C:7]([C:9]2[CH:17]=[C:16]3[C:12]([C:13]([C:26]4[N:30](COCC[Si](C)(C)C)[C:29]5[CH:39]=[CH:40][CH:41]=[CH:42][C:28]=5[N:27]=4)=[N:14][N:15]3COCC[Si](C)(C)C)=[CH:11][CH:10]=2)[CH:8]=1.COC1C(OCOCC[Si](C)(C)C)=CC(C)=C(C2C=C3C(C(C4N(COCC[Si](C)(C)C)C5C=CC=CC=5N=4)=NN3COCC[Si](C)(C)C)=CC=2)C=1>>[NH:30]1[C:29]2[CH:39]=[CH:40][CH:41]=[CH:42][C:28]=2[N:27]=[C:26]1[C:13]1[C:12]2[C:16](=[CH:17][C:9]([C:7]3[CH:8]=[C:3]([O:2][CH3:1])[C:4]([OH:45])=[CH:5][C:6]=3[CH2:43][OH:44])=[CH:10][CH:11]=2)[NH:15][N:14]=1

Participants

3

Reactant 2

HCID 218773976-[5-methoxy-2-methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-(2-trimethylsilanyl-ethoxymethyl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1H-indazoleHCID 218774016-[5-methoxy-2-hydroxymethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-(2-trimethylsilanyl-ethoxymethyl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1H-indazole

Product 1

HCID 1361649533-1H-Benzoimidazol-2-yl-6-(2-(hydroxymethyl)-5-methoxy-4-hydroxy-phenyl)-1H-indazole

Procedure

Example 24(n) was prepared in a similar manner to that described for Example 24(a), except that 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, prepared as described below, was used instead of 6-[5-methoxy-2-methyl-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-(2-trimethylsilanyl-ethoxymethyl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzoimidazol-2-yl]-1H-indazole. 1H NMR (300 MHz, DMSO-d6) δ 13.59 (s, 1H), 12.95 (s, 1H), 9.05 (s, 1H), 8.49 (d, 1H, J=8.4 Hz), 7.72 (dd, 1H, J=6.3, 2.1 Hz), 7.60 (s, 1H), 7.51 (dd, 1H, J=6.3, 2.1 Hz), 7.31 (d, 1H, J=8.4 Hz), 7.20–7.24 (m, 2H), 7.02 (s, 1H), 6.87 (s, 1H), 5.02 (t, 1H, J=5.4 Hz), 4.32 (d, 2H, J=5.4 Hz), 3.80 (s, 3H). MS (ES) [m+H]/z calc'd 387. found 387. [m−H]/z calc'd 385. found 385.

Workup

  1. customExample 24(n) was prepared in a similar manner to that
  2. customprepared

Sources & evidence

ORD record
ord-f245e392c03d498fa4fb0d624010d908
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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