(2,4-Dimethylphenyl)boronic acid → 2-(2,4-Dimethylphenyl)-N,N-dipropylimidazo[1,2-a]pyridin-5-amine

Temperature

50 °C

2-Bromo-N,N-dipropylimidazo[1,2-a]pyridin-5-amine (prepared in example 61) (0.17 g, 0.57 mmol) was dissolved in 1,2-dimethoxyethane (DME) (1.5 mL). Pd(PPh3)4 (0.033 g, 0.028 mmol) was added and the reaction was stirred at 50° C. for 15 minutes. The solution was cooled and 2,4-dimethylphenylboronic acid (0.103 g, 0.69 mmol) in DME (1 mL) was added to the reaction mixture. KOtBu (0.128 g, 1.14 mmol) in tBuOH (1 mL) was also added to the reaction. The reaction was heated to 100° C. for 1 hr. The solution was filtered through paper and concentrated. Crude material was purified via reverse phase HPLC (acetonitrile containing 0.1% TFA/water containing 0.1% TFA) to obtain 3.1 mg of the title compound (2% yield).

1. temperatureThe solution was cooled
2. temperatureThe reaction was heated to 100° C. for 1 hr
3. filtrationThe solution was filtered through paper
4. concentrationconcentrated
5. customCrude material was purified via reverse phase HPLC (acetonitrile containing 0.1% TFA/water containing 0.1% TFA)

ORD record

ord-69501b768d5d4a489bb84aaecbbae6a8

Source dataset

uspto-grants-2010_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07714009B2