Cesium carbonate → HCID 58190548, compound

HRID 1892414Notes

Reaction equation

HRID 1892414 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=2.[CH3:17][N:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1.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.[Cs+].[Cs+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:17][N:18]1[CH2:23][CH2:22][N:21]([C:2]2[CH:3]=[N:4][C:5]3[C:10]([CH:11]=2)=[CH:9][C:8]([CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:7][CH:6]=3)[CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 531671-MethylpiperazineHCID 634876Binap, (A+-)-HCID 58190594HCID 58190594, compound

Product 1

HCID 58190548HCID 58190548, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Procedure

A solution of methyl 2-(3-bromoquinolin-6-yl)acetate (1.0 g, 3.57 mmol), 1-methylpiperazine (0.429 g, 4.28 mmol), Pd2(dba)3 (65 mg, 0.071 mmol), BINAP (133 mg, 0.214 mmol) and Cs2CO3 (1.628 g, 5.00 mmol) in 10 mL of toluene was heated at 100° C. for 18 h. After cooling, the solid was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by flash chromatography in silica gel eluting with a EtOAC/hexane gradient to afford 599 mg (56%) of the title compound as a yellow solid. 1H-NMR (400 MHz, CDCl3) δ ppm 8.77 (s, 1H), 7.94 (d, 1H), 7.57 (s, 1H), 7.42 (d, 1H), 7.30 (s, 1H), 3.78 (s, 2H), 3.72 (s, 3H), 3.41-3.33 (m, 4H), 2.65-2.63 (m, 4H), 2.39 (s, 3H). LCMS (method A): [MH]+=300, tR=2.06 min.

Workup

  1. temperatureAfter cooling
  2. customthe solid was removed by filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by flash chromatography in silica gel eluting with a EtOAC/hexane gradient

Sources & evidence

ORD record
ord-6621567b7e5742dcb1aa6ef8f0541625
Source dataset
uspto-grants-2013_08
Patent number
US08507676B2

Reaction notes

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