Imidazole → HCID 59418657, compound

HRID 1896557Notes

Reaction equation

HRID 1896557 reaction equation
N1C=CN=C1.[Br:6][C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][CH2:12]/[C:13]/2=[N:16]/[OH:17])=[CH:9][CH:8]=1.[CH:18]([Si:21](Cl)([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])([CH3:20])[CH3:19]>C(Cl)Cl>[CH:18]([Si:21]([CH:25]([CH3:27])[CH3:26])([CH:22]([CH3:24])[CH3:23])[O:17]/[N:16]=[C:13]1/[CH2:12][CH2:11][C:10]2[C:14]/1=[CH:15][C:7]([Br:6])=[CH:8][CH:9]=2)([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 139400Triisopropylsilyl chlorideHCID 59418675HCID 59418675, compound

Product 1

HCID 59418657HCID 59418657, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of imidazole (11 g, 162 mmol) in 100 mL of dry DCM was added dropwise to a solution of (Z)-6-bromo-2,3-dihydro-1H-inden-1-one oxime (1C) (18.2 g, 81 mmol) and triisopropylsilyl chloride (23.3 g, 121.5 mmol) in solution in 40 mL of dry DCM. The reaction mixture was stirred for 16 hours at rt. It was then filtered to remove the precipitate and the filtrate was concentrated under vacuum. The crude material was purified by column chromatography on silica gel to provide (Z)-6-bromo-2,3-dihydro-1H-inden-1-one O-triisopropylsilyl oxime (1D). The crude product was taken on to the next step immediately.

Workup

  1. filtrationIt was then filtered
  2. customto remove the precipitate
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe crude material was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e7963545ee63442ba6253d0f015c88f4
Source dataset
uspto-grants-2013_08
Patent number
US08518970B2

Reaction notes

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