Cesium carbonate → HCID 44612352, compound

HRID 1257122Notes

Reaction equation

HRID 1257122 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15](=[O:18])[NH:16][CH3:17])[CH2:11][CH2:10]2)[CH:5]=[CH:4][N:3]=1.[NH2:19][C:20]1[N:21]=[CH:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=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][NH:16][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:19][C:20]3[N:21]=[CH:22][C:23]4[C:28]([CH:29]=3)=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:7]=2)[CH2:10][CH2:11]1)=[O:18]

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 58285194HCID 58285194, compound

Product 1

HCID 44612352HCID 44612352, compound

Reagents, catalysts & solvents 3

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

Procedure

1-(2-Chloro-pyridin-4-ylmethyl)-4-(N-methylcarbamoyl)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 (63 mg, 28% yield): 1H NMR (CDCl3, 300 MHz) δ: 2.49 (t, J=4.4 Hz, 4H, PyridylCH2NCH2CH2), 2.83 (s, 6H, N(CH3)2), 3.29 (t, J=4.8 Hz, 4H, NCH2CO), 3.52 (s, 2H, pyridylCH2), 6.88-8.98 (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-667e282e571e40b39683f0a3a6d34a70
Source dataset
uspto-grants-2013_06
Patent number
US08461339B2

Reaction notes

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