Imidazole → HCID 68526105, compound

HRID 222465Notes

Reaction equation

HRID 222465 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([CH2:9][C:10]([NH2:12])=[O:11])=[CH:7][O:8][C:4]=2[CH:3]=1.ClCCl.N1C=CN=C1.[C:23]([Si:27]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)Cl)([CH3:26])([CH3:25])[CH3:24]>CN(C=O)C>[C:23]([Si:27]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[O:1][C:2]1[CH:14]=[CH:13][C:5]2[C:6]([CH2:9][C:10]([NH2:12])=[O:11])=[CH:7][O:8][C:4]=2[CH:3]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6344DichloromethaneHCID 94078tert-ButyldiphenylchlorosilaneHCID 59140641HCID 59140641, compound

Product 1

HCID 68526105HCID 68526105, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(6-hydroxy-benzofuran-3-yl)-acetamide (0.23 g, 1.20 mmol) in a mixture of dry dichloromethane (20 mL) and DMF (6 mL) was added imidazole (0.34 g, 5.05 mmol), followed by tert-butyldiphenylchlorosilane (1.31 mL, 5.05 mmol) at room temperature and the mixture was stirred for two days. The solution was quenched with methanol and stirred for 10 min. The solvent was evaporated in vacuo and the residue was purified by column chromatography (methanol:dichloromethane; 5:95) to give the 2-[6-(tert-butyl-diphenyl-silanyloxy)-benzofuran-3-yl]-acetamide as a white solid (0.40 g, 78%). 1H NMR (DMSO-d6, 400 MHz) 1.06 (s, 9H), 3.38 (s, 2H), 6.74 (dd, J=1.8, 8.4 Hz, 1H), 6.80 (d, J=1.8 Hz, 1H), 7.40 (d, J=8.4 Hz, 1H), 7.42-7.54 (m, 7H), 7.64 (s, 1H), 7.70 (m, 4H), 7.80 (s, 1H).

Workup

  1. customThe solution was quenched with methanol
  2. stirringstirred for 10 min
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified by column chromatography (methanol:dichloromethane; 5:95)

Sources & evidence

ORD record
ord-c689a15f82d54345beb91b07af9642bd
Source dataset
uspto-grants-2012_06
Patent number
US08207216B2

Reaction notes

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