Trityl chloride → 4-Iodo-1-tritylimidazole
反応式
[I:1][C:2]1[NH:6][CH:5]=[N:4][CH:3]=1.IC1NC=CN=1.[C:13]1([C:19](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>>[C:13]1([C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[N:4]2[CH:3]=[C:2]([I:1])[N:6]=[CH:5]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1参加物
実験手順
As depicted in Scheme II, imidazole was reacted with iodine under basic conditions at reduced temperature in an appropriate solvent, yielding a mixture of iodoimidazoles (v), for example, 2,4,5-triiodoimidazole and 2,5-diiodoimidazole. The mixture of iodoimidazole derivatives (v) was then treated with aqueous sodium sulfite at elevated temperature in an appropriate solvent, yielding a single iodo derivative (vi), for example, 5-iodoimidazole. The free amine in the 1-position of the iodoimidazole (vi) ring was then protected by reacting it with triphenylmethyl chloride under basic conditions in an appropriate solvent, affording the corresponding 1-(triphenylmethyl)-4-iodoimidazole (vii). The iodoimidazole (vii) was in turn treated with ethylmagnesium bromide in an appropriate solvent, then reacted with an appropriate cyclic ketone (ii), for example, 6-methoxy-5-methylindan-1-one (X is —CHR17—), affording the corresponding 1,2-unsaturated heterocyclic derivative (viii), for example, 3-(imidazol-5-yl)-5-methoxy-6-methylindene. Heterocyclic derivative (viii) was then hydrogenated under conditions set forth above, yielding the corresponding compounds of formula (I), for example, 1-(imidazol-5-yl)-6-methoxy-5-methylindane. Example 4 set forth below provides in detail the synthesis route shown in Scheme II.
出典と根拠
- ORDレコード
- ord-f59236ac68384445a30367f7b662acfc
- 出典データセット
- uspto-grants-2008_08
- 特許番号
- US07417057B2
反応ノート
読み込み中…