Sodium Carbonate → HCID 57990339, compound

HRID 2381770Notes

Reaction equation

HRID 2381770 reaction equation
Br[C:2]1[C:3]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:11][CH2:10]2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[N:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:8][C:5]1[N:4]=[C:3]([N:9]2[CH2:14][CH2:13][CH:12]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:11][CH2:10]2)[C:2]([C:27]2[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=2)=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 57990385HCID 57990385, compound

Product 1

HCID 57990339HCID 57990339, compoundYield 35.1%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of tert-butyl (1-(5-bromo-2-chloropyrimidin-4-yl)piperidin-4-yl)methylcarbamate (229 mg, 0.564 mmol), pyridine-4-boronic acid (76 mg, 0.618 mmol) and Pd(Ph3P)2Cl2 (40 mg, 0.056 mmol) in dioxane (3 mL), aq. Na2CO3 (180 mg, 1.69 mmol) (1.0 mL) was added. The mixture was stirred at 100° C. for 20 h. It was concentrated in vacuo. The residue was purified by HPLC to give tert-butyl (1-(2-chloro-5-(pyridin-4-yl)pyrimidin-4-yl)piperidin-4-yl)methylcarbamate (80 mg).

Workup

  1. additionwas added
  2. concentrationIt was concentrated in vacuo
  3. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-5de7bdf32ae8451095d9451bce3fe1e8
Source dataset
uspto-grants-2012_09
Patent number
US08258144B2

Reaction notes

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