Imidazole → HCID 58928746, compound

HRID 853610Notes

Reaction equation

HRID 853610 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][N:7]2[C:20](=[O:21])[C:19]3[C:18]([OH:22])=[C:17]4[C:12]([CH:13]=[CH:14][CH:15]=[N:16]4)=[CH:11][C:10]=3[CH2:9][C:8]2=[O:23])=[CH:4][CH:3]=1.Cl[Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29].N1C=CN=C1>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:20](=[O:21])[C:19]3[C:18]([O:22][Si:27]([CH:34]([CH3:36])[CH3:35])([CH:31]([CH3:33])[CH3:32])[CH:28]([CH3:30])[CH3:29])=[C:17]4[C:12]([CH:13]=[CH:14][CH:15]=[N:16]4)=[CH:11][C:10]=3[CH2:9][C:8]2=[O:23])=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 58928864HCID 58928864, compound

Product 1

HCID 58928746HCID 58928746, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

For example, 7-(4-fluoro-benzyl)-9-hydroxy-5H-1,7-diaza-anthracene-6,8-dione A1.6 is reacted with one molar equivalent of chlorotriisopropylsilane and imidazole in dimethylformamide at ambient temperature, as described in Tet. Lett., 2865, 1974, to produce 7-(4-fluoro-benzyl)-9-triisopropylsilanyloxy-5H-1,7-diaza-anthracene-6,8-dione A1.7. The product is then reacted in dimethylformamide solution at about 60° C. with one molar equivalent of a dialkyl 2-bromoethyl phosphonate A1.8 (Aldrich) and lithium hexamethyldisilazide, to yield the alkylated product A1.9. The silyl protecting group is then removed by reaction with tetrabutylammonium fluoride in tetrahydrofuran, as described in J. Org. Chem., 51, 4941, 1986, to give the phenolic product A1.10.

Sources & evidence

ORD record
ord-55153deafb534aed9fbfaf58daeac125
Source dataset
uspto-grants-2007_08
Patent number
US07253180B2

Reaction notes

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