3-Pyridinylboronic acid → tert-butyl {2-[2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}carbamate
Reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][CH2:8][CH2:9][N:10]1[C:22]2[C:21]3[CH:20]=[CH:19][C:18](Br)=[CH:17][C:16]=3[N:15]=[C:14](N)[C:13]=2[N:12]=[C:11]1[CH2:25][O:26][CH2:27][CH3:28])([CH3:4])([CH3:3])[CH3:2].[N:30]1[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[CH:31]=1>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:27]([O:26][CH2:25][C:11]1[N:10]([CH2:9][CH2:8][NH:7][C:6](=[O:29])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[C:22]2[C:21]3[CH:20]=[CH:19][C:18]([C:32]4[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=4)=[CH:17][C:16]=3[N:15]=[CH:14][C:13]=2[N:12]=1)[CH3:28]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
tert-Butyl[2-(4-amino-7-bromo-2-ethoxymethyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate (21.80 g, 46.94 mmol) and 3-pyridylboronic acid (6.64 g, 54.0 mmol) were coupled according to the method described in Part J of Example 1. Palladium (II) acetate was added as a 5 mg/mL solution in toluene. The reaction was terminated after 4.5 hours, and the work-up procedure described in Part F of Examples 125–135 was followed. The crude product was recrystallized from acetonitrile (12 mL/g) to provide 10.80 g of tert-butyl {2-[2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}carbamate as a white solid.
Workup
- customThe reaction was terminated after 4.5 hours
- customThe crude product was recrystallized from acetonitrile (12 mL/g)
Sources & evidence
- ORD record
- ord-b4129340568849b5959a9ea21a3b9236
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07091214B2
Reaction notes
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