Cesium carbonate → HCID 44612467, compound

HRID 1257123Notes

Reaction equation

HRID 1257123 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:19])[N:16]([CH3:18])[CH3:17])[CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1.[NH2:20][C:21]1[N:22]=[CH:23][C:24]2[C:29]([CH:30]=1)=[CH:28][CH:27]=[CH:26][CH:25]=2.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.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].CCOC(C)=O>[CH3:17][N:16]([CH3:18])[C:15]([N:12]1[CH2:13][CH2:14][N:9]([CH2:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:20][C:21]3[N:22]=[CH:23][C:24]4[C:29]([CH:30]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)[CH:7]=2)[CH2:10][CH2:11]1)=[O:19]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 311869Isoquinolin-3-AmineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 58285186HCID 58285186, compound

Product 1

HCID 44612467HCID 44612467, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(2-Chloro-pyridin-4-ylmethyl)-4-(N,N-dimethylcarbamoyl)piperazine (1.0 equiv) (Preparation B-12) was mixed with 3-aminoisoquinoline (1.0 equiv), Pd2(dba)3(0.1 equiv), xantphos (0.15 equiv), and Cs2CO3 (1.4 equiv) in toluene. The mixture was refluxed overnight, and EtOAc was added in to dilute the mixture. After filtration, the filtrate was concentrated and applied onto a silica gel column. The title compound was obtained as a yellow solid (50 mg, 22% yield): 1H NMR (CDCl3, 300 MHz) δ: 2.47 (t, J=5.0 Hz, 4H, PyridylCH2NCH2CH2), 2.83 (d, J=4.8 Hz, 3H, NHCH3), 3.41 (t, J=5.0 Hz, 4H, NCH2CO), 3.51 (s, 2H, pyridylCH2), 6.86-8.99 (m, 9H, isoquinolyl+pyridyl).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. additionto dilute the mixture
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-521ba77a277d4f6f93bf7d7336da25df
Source dataset
uspto-grants-2013_06
Patent number
US08461339B2

Reaction notes

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