(2-Methoxyethyl)(methyl)amine → HCID 70663212, compound

HRID 877982Notes

Reaction equation

HRID 877982 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([NH:8][CH3:9])=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH:3]=1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[CH3:69][O:70][CH2:71][CH2:72][NH:73][CH3:74]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:69][O:70][CH2:71][CH2:72][N:73]([CH3:74])[C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[C:5]([NH:8][CH3:9])=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 577104436-chloro-N-methyl-4-(2-methylphenyl)pyridin-3-amine

Product 1

HCID 70663212HCID 70663212, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
150 °C

Procedure

6-Chloro-N-methyl-4-o-tolylpyridin-3-amine (60 mg, 0.26 mmol, prepared as described in WO2005/002577), sodium tert-butoxide (74 mg, 0.77 mmol), palladium acetate (5.8 mg, 0.026 mmol, CAS RN 3375-31-3) and BINAP (48 mg, 0.077 mmol, CAS RN 76189-55-4) were dissolved in toluene (3 mL) and stirred under an argon atmosphere for 10 minutes. N-(2-Methoxyethyl)methylamine (46 mg, 0.52 mmol, CAS RN 38256-93-8) was added and the reaction mixture was sealed and heated to 150° C. under microwave irradiation for 30 min. The reaction mixture was columned directed on silica gel (EtOAc) to yield the product as a light brown oil (36 mg, 49%). This material was used in the next step without further purification.

Workup

  1. customthe reaction mixture was sealed

Sources & evidence

ORD record
ord-f834ac4dde084890ac4352dd696b3728
Source dataset
uspto-grants-2015_03
Patent number
US08987307B2

Reaction notes

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