Sodium Carbonate → HCID 67125474, compound

HRID 1470763Notes

Reaction equation

HRID 1470763 reaction equation
C([O-])([O-])=O.[Na+].[Na+].B(O)(O)[C:8]1[CH:13]=[CH:12][C:11]2[O:14][CH2:15][O:16][C:10]=2[CH:9]=1.Cl[C:20]1[N:25]=[C:24]([N:26]2[CH2:31][CH2:30][CH:29]([C:32]3[CH:37]=[CH:36][C:35]([C@@H:38]([NH:40][C:41](=[O:43])[CH3:42])[CH3:39])=[CH:34][CH:33]=3)[CH2:28][CH2:27]2)[CH:23]=[CH:22][N:21]=1>O1CCOCC1.CN(C=O)C.O.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>[O:14]1[C:11]2[CH:12]=[CH:13][C:8]([C:20]3[N:25]=[C:24]([N:26]4[CH2:31][CH2:30][CH:29]([C:32]5[CH:37]=[CH:36][C:35]([C@@H:38]([NH:40][C:41](=[O:43])[CH3:42])[CH3:39])=[CH:34][CH:33]=5)[CH2:28][CH2:27]4)[CH:23]=[CH:22][N:21]=3)=[CH:9][C:10]=2[O:16][CH2:15]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 86666708HCID 86666708, compound

Product 1

HCID 67125474HCID 67125474, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolventHCID 21962138N,N-Dimethylformamide--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

Under argon atmosphere 0.2 mL Na2CO3-solution (2 mol/L) and 3 mg (0.004 mmol) bis(triphenylphosphine)-palladium(II) chloride are added to a mixture of 50 mg (0.30 mmol) 3,4-(methylenedioxy)phenylboronic acid and 36 mg (0.10 mmol) (S)—N-(1-{4-[1-(2-chloro-pyrimidin-4-yl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide (compound XIV.3) in 2 mL dioxane/1 mL MeOH. The mixture is stirred at 90° C. for 3 h. After that time, the mixture is diluted with DMF/water and is filtered. The filtrate is purified using reversed phase HPLC (water (+0.1% TFA)/MeOH) to yield the desired product.

Workup

  1. filtrationis filtered
  2. customThe filtrate is purified

Sources & evidence

ORD record
ord-33accf83085148cd9d6c43049f27f0ee
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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