3-Pyridinylboronic acid → tert-butyl {2-[2-butyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}carbamate

HRID 9438Notes

Reaction equation

HRID 9438 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][CH2:26][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>>[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]([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]=[C:11]1[CH2:25][CH2:26][CH2:27][CH3:28])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 27343783-Pyridinylboronic acidHCID 86593766tert-Butyl [2-(4-amino-7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate

Product 1

HCID 86593765tert-butyl {2-[2-butyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}carbamateYield 83.2%

Procedure

tert-Butyl[2-(4-amino-7-bromo-2-butyl-1H-imidazo[4,5-c]quinolin-1-yl)ethyl]carbamate (14.09 g, 30.5 mmol) and 3-pyridylboronic acid (4.31 g, 35.0 mmol) were coupled according to the method described in Part G of Example 386. The reaction was heated for 2.5 hours. The crude product was triturated with toluene (15 mL/g) at 123° C. and isolated by filtration to provide 11.31 g of tert-butyl{2-[2-butyl-7-(pyridin-3-yl)-1H-imidazo[4,5-c]quinolin-1-yl]ethyl}carbamate as a white solid.

Workup

  1. temperatureThe reaction was heated for 2.5 hours
  2. customThe crude product was triturated with toluene (15 mL/g) at 123° C.
  3. customisolated by filtration

Sources & evidence

ORD record
ord-bd2e3b5bb7384ffca222305e95fc44cb
Source dataset
uspto-grants-2006_08
Patent number
US07091214B2

Reaction notes

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