Binap, (A+-)- → N-(5,6'-dimethyl-2,2'-bipyridin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-7-amine

HRID 1522574Notes

Reaction equation

C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.I[C:48]1[C:49]2[C:50](=[CH:54][N:55]([CH2:57][C:58]3[CH:63]=[CH:62][C:61]([O:64][CH3:65])=[CH:60][CH:59]=3)[N:56]=2)[N:51]=[CH:52][CH:53]=1.[CH3:66][C:67]1[C:68]([NH2:80])=[CH:69][C:70]([C:73]2[CH:78]=[CH:77][CH:76]=[C:75]([CH3:79])[N:74]=2)=[N:71][CH:72]=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C(O[Pd]OC(=O)C)(=O)C>[CH3:66][C:67]1[C:68]([NH:80][C:48]2[CH:53]=[CH:52][N:51]=[C:50]3[CH:49]=[N:56][N:55]([CH2:57][C:58]4[CH:59]=[CH:60][C:61]([O:64][CH3:65])=[CH:62][CH:63]=4)[C:54]=23)=[CH:69][C:70]([C:73]2[CH:78]=[CH:77][CH:76]=[C:75]([CH3:79])[N:74]=2)=[N:71][CH:72]=1

Participants

Conditions

Temperature: 40 °C

Procedure

(R)-BINAP (0.478 g, 0.767 mmol) and diacetoxypalladium (0.040 g, 0.178 mmol) were combined in toluene (8 mL) and stirred at 40° C. for 10 minutes. 7-Iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine (0.65 g, 1.780 mmol) suspended in toluene (5 mL), 5,6′-dimethyl-2,2′-bipyridin-4-amine (0.355 g, 1.780 mmol) and sodium 2-methylpropan-2-olate (0.257 g, 2.67 mmol) were added. Nitrogen was sparged into the solution for about 2 minutes, and the reaction was heated at 100° C. overnight. The reaction was then cooled to give a solution of N-(5,6′-dimethyl-2,2′-bipyridin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-7-amine which was used as is in the next step.

Workup

customNitrogen was sparged into the solution for about 2 minutes
temperaturethe reaction was heated at 100° C. overnight
temperatureThe reaction was then cooled

Sources & evidence

ORD record: ord-f1c7ddc1a3604e0a96e655665c4f9522
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073918B2

Reaction notes

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