Potassium Phosphate, Tribasic → (2-(2-(4-Methoxybenzylamino)-3-morpholinoquinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone

HRID 1028936Notes

Reaction equation

HRID 1028936 reaction equation
C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.Br[C:36]1[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:37]=1[C:43]([N:45]1[CH2:49][CH2:48][CH2:47][CH2:46]1)=[O:44].[CH3:50][O:51][C:52]1[CH:84]=[CH:83][C:55]([CH2:56][NH:57][C:58]2[C:67]([N:68]3[CH2:73][CH2:72][O:71][CH2:70][CH2:69]3)=[CH:66][C:65]3[C:60](=[CH:61][CH:62]=[C:63](B4OC(C)(C)C(C)(C)O4)[CH:64]=3)[N:59]=2)=[CH:54][CH:53]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[CH3:50][O:51][C:52]1[CH:53]=[CH:54][C:55]([CH2:56][NH:57][C:58]2[C:67]([N:68]3[CH2:69][CH2:70][O:71][CH2:72][CH2:73]3)=[CH:66][C:65]3[C:60](=[CH:61][CH:62]=[C:63]([C:36]4[C:41]([CH3:42])=[CH:40][CH:39]=[CH:38][C:37]=4[C:43]([N:45]4[CH2:49][CH2:48][CH2:47][CH2:46]4)=[O:44])[CH:64]=3)[N:59]=2)=[CH:83][CH:84]=1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 665791491-(2-Bromo-3-methylbenzoyl)pyrrolidineHCID 71253458N-(4-methoxybenzyl)-3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine

Product 1

HCID 71253303(2-(2-(4-Methoxybenzylamino)-3-morpholinoquinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (47.8 mg, 0.10 mmol), (2-bromo-3-methylphenyl)(pyrrolidin-1-yl)methanone (323 mg, 1.2 mmol), N-(4-methoxybenzyl)-3-morpholino-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (477 mg, 1.0 mmol), Pd2(dba)3 (45.9 mg, 0.050 mmol), K3PO4 (0.25 mL, 3.0 mmol), and 1,4-dioxane (7 mL)/water (3.50 mL) was heated in a microwave at 140° C. for 12 min. The reaction mixture was filtered then concentrated in vacuo. The crude product was purified by silica flash chromatography (0-10% MeOH/DCM) to give (2-(2-(4-methoxybenzylamino)-3-morpholinoquinolin-6-yl)-3-methylphenyl)(pyrrolidin-1-yl)methanone as an orange oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthen concentrated in vacuo
  3. customThe crude product was purified by silica flash chromatography (0-10% MeOH/DCM)

Sources & evidence

ORD record
ord-aea5f11ccac94ff7a2798af51f83a995
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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