Imidazole → HCID 68408912, compound

HRID 1157072Notes

Reaction equation

HRID 1157072 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[CH:23]=[CH:22][C:14]([O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][OH:21])=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[CH3:24][C:25]([Si:28](Cl)([CH3:30])[CH3:29])([CH3:27])[CH3:26].N1C=CN=C1>ClCCl>[C:25]([Si:28]([CH3:30])([CH3:29])[O:21][CH2:20][CH2:19][O:18][CH2:17][CH2:16][O:15][C:14]1[CH:13]=[CH:12][C:11]([CH:10]=[CH:9][C:6]2[CH:5]=[CH:4][C:3]([NH:2][CH3:1])=[CH:8][CH:7]=2)=[CH:23][CH:22]=1)([CH3:27])([CH3:26])[CH3:24]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 68408129HCID 68408129, compound

Product 1

HCID 68408912HCID 68408912, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 3a (45 mg, 0.14 mmol) and TBDMSCl (33 mg, 0.22 mmol) were dissolved in dichloromethane (10 ml) followed by imidazole (20 mg, 0.29 mmol). The solution was stirred at room temperature for 2 hours. After standard workup with dichloromethane, the residue was purified by silica gel column chromatography (1.5% methanol in dichloromethane) to afford 7a (56 mg, 91%): 1H NMR δ 7.40 (m, 4H), 6.90 (m, 4H), 6.75 (d, 2H, J=7.9 Hz), 4.15 (t, 2H), 3.88 (t, 2H), 3.82 (t, 2H), 3.66 (t, 2H), 2.85 (s, 3H), 0.92 (s, 9H), 0.09 (s, 6H).

Workup

  1. customAfter standard workup with dichloromethane, the residue was purified by silica gel column chromatography (1.5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-464a7899678d4d34b2c447cb9e864b86
Source dataset
uspto-grants-2010_10
Patent number
US07807135B2

Reaction notes

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