Sodium Carbonate → HCID 178483459, compound

HRID 1743791Notes

Reaction equation

HRID 1743791 reaction equation
[N:1]1[CH:6]=[CH:5][C:4](B(O)O)=[CH:3][CH:2]=1.Br[C:11]1[CH:12]=[N:13][C:14]([N:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([C:25]#[C:26][CH2:27][N:28]([CH3:30])[CH3:29])[CH2:21][CH2:20]2)[CH3:18])=[N:15][CH:16]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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]>[CH3:30][N:28]([CH3:29])[CH2:27][C:26]#[C:25][C@H:22]1[CH2:21][CH2:20][C@H:19]([N:17]([CH3:18])[C:14]2[N:13]=[CH:12][C:11]([C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[CH:16][N:15]=2)[CH2:24][CH2:23]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 178483457HCID 178483457, compound

Product 1

HCID 178483459HCID 178483459, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
85 °C

Procedure

In this reaction, the solvents were degased with argon for 10 minutes. A suspension of 7.3 mg PdCl2(dppf), of 29.4 mg (0.24 mmol) of 4-pyridylboronic acid an of 70 mg (0.2 mmol) of trans-(5-Bromo-pyrimidin-2-yl)-[4-(3-dimethylamino-prop-1-ynyl)-cyclohexyl]-methyl-amine in 3.5 ml dioxane were treated with 1 ml of an aqueous solution of 2M Na2CO3. After 17 h at 85° C., 7 mg of PdCl2(dppf) were added and the reaction was heated further at 85° C. for 24 h. The mixture was partitioned between aqueous saturated NaHCO3/Et2O (3×) and the combined organic phases were extracted with 0.1M HCl. The HCl-phase was adjusted to pH 14 (1 N NaOH) and extracted with Et2O (3×). The organic phase was washed with 10% NaCl and dried over Na2SO4 to yield after purifiction with flash-chromatography on silica gel (CH2Cl2/MeOH 99:1 to 9:1) 9 mg (13%) of trans-[4-(3-Dimethylamino-prop-1-ynyl)-cyclohexyl]-methyl-(5-pyridin-4-yl-pyrimidin-2-yl)-amine, MS: 350 (MH+).

Workup

  1. customIn this reaction
  2. customthe solvents were degased with argon for 10 minutes
  3. additionA suspension of 7.3 mg PdCl2(dppf)
  4. customThe mixture was partitioned between aqueous saturated NaHCO3/Et2O (3×)
  5. extractionthe combined organic phases were extracted with 0.1M HCl
  6. extractionextracted with Et2O (3×)
  7. washThe organic phase was washed with 10% NaCl
  8. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-efdfa650515746f7b9d9dea24add8fba
Source dataset
uspto-grants-2006_03
Patent number
US07012077B2

Reaction notes

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