1-Methylimidazole → HCID 9891739, compound

HRID 273301Notes

Reaction equation

HRID 273301 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[CH:3]1.C([Li])CCC.Cl[Si](CC)(CC)CC.[Cl:20][C:21]1[CH:47]=[CH:46][C:24]([C:25]([C:27]2[CH:28]=[C:29]3[C:34](=[CH:35][CH:36]=2)[N:33]([CH3:37])[C:32](=[O:38])[CH:31]=[C:30]3[C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=2)=[O:26])=[CH:23][CH:22]=1>O1CCCC1.CCCCCC>[OH:26][C:25]([C:24]1[CH:23]=[CH:22][C:21]([Cl:20])=[CH:47][CH:46]=1)([C:6]1[N:2]([CH3:1])[CH:3]=[N:4][CH:5]=1)[C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[N:33]([CH3:37])[C:32](=[O:38])[CH:31]=[C:30]2[C:39]1[CH:44]=[CH:43][CH:42]=[C:41]([Cl:45])[CH:40]=1

Participants

7

Reactant 4

HCID 13901-MethylimidazoleHCID 13819ChlorotriethylsilaneHCID 114525536-(4-Chlorobenzoyl)-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinoneHCID 178418339Butyllithium2×

Product 1

HCID 9891739HCID 9891739, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Procedure

Herein, in step 1, the intermediate 1-methyl imidazole in tetrahydrofuran, is mixed with a solution of n-butyllithium in a hexane solvent to which is added chlorotriethylsilane (triethylsilyl chloride), followed by a further addition of n-butyllithium in hexane, the resulting mixture being cooled to −78° C. before the addition of a solution of a compound of formula (I), i.e. 6-(4-chlorobenzoyl)-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone in tetrahydrofuran. The reaction mixture is subsequently brought to room temperature, and then hydrolysed, extracted with ethyl acetate and the organic layer worked up to obtain a compound of formula (II), i.e. (±)-6-[hydroxy (4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-4-(3-chlorophenyl)-1-methyl-2(1H)-quinolinone.

Workup

  1. customis subsequently brought to room temperature
  2. extractionhydrolysed, extracted with ethyl acetate

Sources & evidence

ORD record
ord-88db2d539c3e4099b2d5005ab6e92d8a
Source dataset
uspto-grants-2008_11
Patent number
US07456287B2

Reaction notes

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