Sodium Bicarbonate → HCID 67970837, compound

HRID 1470762Notes

Reaction equation

HRID 1470762 reaction equation
Cl[C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]=[C:4]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[CH:25]=[CH:24][C:23]([C@@H:26]([NH:28][C:29](=[O:31])[CH3:30])[CH3:27])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)[N:3]=1.[CH3:32]B1OB(C)OB(C)O1.C([O-])(O)=O.[Na+]>CO.O1CCOCC1.CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH3:32][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:6][N:5]=[C:4]([N:14]2[CH2:19][CH2:18][CH:17]([C:20]3[CH:25]=[CH:24][C:23]([C@@H:26]([NH:28][C:29](=[O:31])[CH3:30])[CH3:27])=[CH:22][CH:21]=3)[CH2:16][CH2:15]2)[N:3]=1

Participants

8

Reactant 3

HCID 516892Sodium BicarbonateHCID 574072Trimethylboroxine2×HCID 86666707HCID 86666707, compound

Product 1

HCID 67970837HCID 67970837, compound

Reagents, catalysts & solvents 4

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalyst2×HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To 43.5 mg (0.10 mmol) (S)—N-(1-{4-[1-(4-chloro-5-phenyl-pyrimidin-2-yl)-piperidin-4-yl]-phenyl}-ethyl)-acetamide (5.50 mmol) in 1 mL MeOH and 2 mL dioxane is added under an argon atmosphere 0.042 mL (0.30 mmol) trimethylboroxine, 0.1 mL NaHCO3 solution (2 mmol/mL) and 2.9 mg (0.0042 mmol) bis(triphenylphosphin)palladium(II)chloride and the mixture is stirred for 3 h at 80° C. After that time, another 100 μL (0.7 mmol) trimethylboroxine and 2.9 mg (0.0042 mmol) bis(triphenylphosphin)-palladium(11)chloride are added and stirring is continued for 12 h at 80° C. The mixture is diluted with DMF, filtered and purified by HPLC (C18 RP Sunfire; water (+0.1% TFA)/MeOH) to yield the desired product.

Workup

  1. stirringstirring
  2. waitis continued for 12 h at 80° C
  3. filtrationfiltered
  4. custompurified by HPLC (C18 RP Sunfire; water (+0.1% TFA)/MeOH)

Sources & evidence

ORD record
ord-c4e5d3f5f51d4c5eafe20badc52f4840
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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