3-Pyridinylboronic acid → tert-butyl {2-[2-ethoxymethyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}carbamate
Reaction equation
N[C:2]1[C:11]2[N:12]=[C:13]([CH2:25][O:26][CH2:27][CH3:28])[N:14]([CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:10]=2[C:9]2[CH:8]=[CH:7][C:6](Br)=[CH:5][C:4]=2[N:3]=1.[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:13]1[N:14]([CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])[C:10]2[C:9]3[CH:8]=[CH:7][C:6]([C:32]4[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=4)=[CH:5][C:4]=3[N:3]=[CH:2][C:11]=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-f97b1ba979e64de0841e2ef5b5dbe074
- Source dataset
- uspto-grants-2009_10
- Patent number
- US07598382B2
Reaction notes
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