Cesium carbonate → HCID 118364802, compound

HRID 1478617Notes

Reaction equation

HRID 1478617 reaction equation
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][N:15]3[C:19]4=[N:20][C:21]([C:24]5[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=5)[C:27]#[N:28])=[CH:22][N:23]=[C:18]4[N:17]=[N:16]3)[CH2:9]2)=[N:6][CH:7]=1.[CH3:32][N:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:45]=[CH:44][C:43](B3OC(C)(C)C(C)(C)O3)=[CH:42][CH:41]=2)[CH2:35][CH2:34]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:32][N:33]1[CH2:38][CH2:37][N:36]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([C:2]3[CH:3]=[N:4][C:5]([N:8]4[CH2:13][CH2:12][O:11][C@H:10]([CH2:14][N:15]5[C:19]6=[N:20][C:21]([C:24]7[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=7)[C:27]#[N:28])=[CH:22][N:23]=[C:18]6[N:17]=[N:16]5)[CH2:9]4)=[N:6][CH:7]=3)=[CH:42][CH:41]=2)[CH2:35][CH2:34]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 467390391-Methyl-4-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl}piperazineHCID 118364736HCID 118364736, compound

Product 1

HCID 118364802HCID 118364802, compoundYield 33%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

(S)-3-(1-((4-(5-bromopyrimidin-2-yl)morpholine-2-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)benzonitrile (30 mg, 0.063 mmol), 1-methyl-4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)benzyl)piperazine (24 mg, 0.094 mmol), Pd(dppf)2Cl2 (2 mg, 0.003 mmol), and Cs2CO3(62 mg, 0.18 mmol) were dissolved in dioxane (4 ml)+H2O (1 ml), and then degassed with N2 (gas), followed by stirring at 80° C. for hours. After the completion of the reaction, the reaction mixture was extracted with H2O, EA, and brine, followed by drying (Na2SO4), filtration, and concentration under reduced pressure, and the residue was purified by column chromatography (MeOH:MC=1:10), to give (S)-3-(1-((4-(5-(4-((4-methylpiperazin-1-yl)methyl)phenyl)pyrimidin-2-yl)morpholine-2-yl)methyl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-6-yl)benzonitrile (12.1 mg, 33%).

Workup

  1. customdegassed with N2 (gas)
  2. customAfter the completion of the reaction
  3. extractionthe reaction mixture was extracted with H2O, EA, and brine
  4. customby drying
  5. filtration(Na2SO4), filtration, and concentration under reduced pressure
  6. customthe residue was purified by column chromatography (MeOH:MC=1:10)

Sources & evidence

ORD record
ord-705f29104fa34c03bb1ca95c47bca030
Source dataset
uspto-grants-2016_08
Patent number
US09403831B2

Reaction notes

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