Chloroform → HCID 86690494, compound

HRID 1026767Notes

Reaction equation

HRID 1026767 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]([CH:16]([CH3:18])[CH3:17])[C:8]([C:10]2[N:11]=[CH:12][N:13]([CH3:15])[CH:14]=2)=[O:9])=[CH:4][C:3]=1B1OC(C)(C)C(C)(C)O1.[CH3:30][C:31]1[N:32]=[CH:33][NH:34][CH:35]=1.C(Cl)(Cl)[Cl:37]>>[ClH:37].[ClH:37].[F:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][N:7]([CH:16]([CH3:17])[CH3:18])[C:8]([C:10]2[N:11]=[CH:12][N:13]([CH3:15])[CH:14]=2)=[O:9])=[CH:4][C:3]=1[N:34]1[CH:35]=[C:31]([CH3:30])[N:32]=[CH:33]1

Participants

4

Reactant 3

HCID 6212ChloroformHCID 86690489HCID 86690489, compoundHCID 178418800HCID 178418800, compound

Product 1

HCID 86690494HCID 86690494, compound

Procedure

A solution of N-[4-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]-1-methyl-N-(propan-2-yl)-1H-imidazole-4-carboxamide (600 mg), 4-methylimidazole (205 mg) and di-μ-hydroxobis[(N,N,N′,N′-tetramethylethylenediamine)copper(II)]dichloride (231 mg) in chloroform (6.0 mL) was stirred under oxygen atmosphere at room temperature for 2 days. The reaction mixture was filtered through Celite, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=75:25-0:100), PTLC(NH silica gel, ethyl acetate) and PTLC (silica gel, chloroform:methanol=19:1). The resulting residue was dissolved in acetonitrile and 4N hydrochloric acid/ethyl acetate (0.08 mL) was added thereto, followed by concentration to afford the title compound (59 mg).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. distillationthe solvent was then distilled off under reduced pressure
  3. customThe resulting residue was purified by column chromatography (NH silica gel cartridge, hexane:ethyl acetate=75:25-0:100), PTLC(NH silica gel, ethyl acetate) and PTLC (silica gel, chloroform:methanol=19:1)
  4. dissolutionThe resulting residue was dissolved in acetonitrile
  5. addition4N hydrochloric acid/ethyl acetate (0.08 mL) was added
  6. concentrationfollowed by concentration

Sources & evidence

ORD record
ord-bcdd6daf725341b6ac147d8f4f774f41
Source dataset
uspto-grants-2014_05
Patent number
US08729271B2

Reaction notes

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