Potassium Carbonate → HCID 58588336, compound

HRID 1361659Notes

Reaction equation

HRID 1361659 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][N:9]=2)=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:14][C:15]1[CH:16]=[C:17]([NH:22][C:23](=[O:32])[C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=2)[CH:18]=[CH:19][C:20]=1[CH3:21].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.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[Cl:31][C:26]1[CH:25]=[C:24]([CH:29]=[CH:28][C:27]=1[Cl:30])[C:23]([NH:22][C:17]1[CH:18]=[CH:19][C:20]([CH3:21])=[C:15]([NH:14][C:2]2[C:7]([C:8]3[CH:13]=[CH:12][N:11]=[CH:10][N:9]=3)=[CH:6][CH:5]=[CH:4][N:3]=2)[CH:16]=1)=[O:32]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 161089744-(2-Chloropyridin-3-yl)pyrimidineHCID 24695862HCID 24695862, compound

Product 1

HCID 58588336HCID 58588336, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

4-(2-Chloro-pyridin-3-yl)-pyrimidine (60 mg, 0.30 mmol), N-(3-amino-4-methyl-phenyl)-3,4-dichloro-benzamide (107 mg, 0.36 mmol), Pd(OAc)2 (4 mg, 0.012 mmol), rac-BINAP (8 mg, 0.012 mmol) and K2CO3 (829 mg, 6.0 mmol) in toluene (3.0 mL) were reacted overnight at 130° C. The reaction was diluted with water and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, filter, concentrated and purified by reverse-phase HPLC (Gilson, acidic mobile phase) yielding the title compound. MS m/z=450, 452 [M]+ and [M+2]+. Calc'd for C23H17Cl2N5O: 450.33.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfilter
  4. concentrationconcentrated
  5. custompurified by reverse-phase HPLC (Gilson, acidic mobile phase)

Sources & evidence

ORD record
ord-4dd918a78eb044fb817628925373a9cc
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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