Imidazole → HCID 68408912, compound

HRID 1257953Notes

Reaction equation

HRID 1257953 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-a5aadfde99c6491785fd8c05a2052b16
Source dataset
uspto-grants-2013_06
Patent number
US08465726B2

Reaction notes

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