Binap, (A+-)- → HCID 67469564, compound

HRID 1522628Notes

Reaction equation

HRID 1522628 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.[F:66][C:67]1[CH:72]=[CH:71][C:70]([F:73])=[CH:69][C:68]=1[C:74]1[N:79]=[C:78]([NH2:80])[C:77]([CH3:81])=[CH:76][N:75]=1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C(O[Pd]OC(=O)C)(=O)C>[F:66][C:67]1[CH:72]=[CH:71][C:70]([F:73])=[CH:69][C:68]=1[C:74]1[N:79]=[C:78]([NH:80][C:48]2[C:49]3[C:50](=[CH:54][N:55]([CH2:57][C:58]4[CH:63]=[CH:62][C:61]([O:64][CH3:65])=[CH:60][CH:59]=4)[N:56]=3)[N:51]=[CH:52][CH:53]=2)[C:77]([CH3:81])=[CH:76][N:75]=1.[F:66][C:67]1[CH:72]=[CH:71][C:70]([F:73])=[CH:69][C:68]=1[C:74]1[N:79]=[C:78]([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)[C:77]([CH3:81])=[CH:76][N:75]=1

Participants

8

Reactant 4

HCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 67469534HCID 67469534, compoundHCID 674695617-Iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine

Product 2

HCID 67469564HCID 67469564, compoundHCID 67470421HCID 67470421, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
40 °C

Procedure

(R)-BINAP (1.396 g, 2.243 mmol), diacetoxypalladium (0.117 g, 0.520 mmol) and toluene (8 mL) were combined and the solution was stirred at 40° C. for 10 minutes. 7-Iodo-2-(4-methoxybenzyl)-2H-pyrazolo[4,3-b]pyridine (1.9 g, 5.20 mmol) suspended in toluene (8 mL), 2-(2,5-difluorophenyl)-5-methylpyrimidin-4-amine (1.151 g, 5.20 mmol) and sodium 2-methylpropan-2-olate (0.750 g, 7.80 mmol) were added and the reaction was then heated at 100° C. overnight. The reaction mixture was cooled, concentrated to give N-(2-(2,5-difluorophenyl)-5-methylpyrimidin-4-yl)-2-(4-methoxybenzyl)-2H-pyrazol[4,3-b]pyridin-7-amine and N-(2-(2,5-difluorophenyl)-5-methylpyrimidin-4-yl)-1-(4-methoxybenzyl)-1H-pyrazolo[4,3-b]pyridin-7-amine which was used without further purification. MS [M+H] found, 459.4.

Workup

  1. temperaturethe reaction was then heated at 100° C. overnight
  2. temperatureThe reaction mixture was cooled
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-44b33ebe56034c2099172bcd89236554
Source dataset
uspto-grants-2015_07
Patent number
US09073918B2

Reaction notes

Loading…