Imidazole → HCID 59418657, compound

HRID 1641045Notes

Reaction equation

HRID 1641045 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 (10). 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-b5a0398d3f774d1aad58f0a02b5b4f8c
Source dataset
uspto-grants-2012_02
Patent number
US08114893B2

Reaction notes

Loading…