Sodium Bicarbonate → HCID 86705195, compound

HRID 2401289Notes

Reaction equation

HRID 2401289 reaction equation
Br[C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[CH2:10][N:11]2[C@@H:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:14][N:13]([C:20]3[CH:21]=[N:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=3)[C:12]2=[O:30])=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:37]([O:39]CC)=[CH2:38])CCC.C(=O)([O-])O.[Na+]>C(#N)C.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.[Cu]I>[C:37]([C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=[O:31])[CH2:10][N:11]2[C@@H:15]([CH2:16][CH:17]([CH3:18])[CH3:19])[CH2:14][N:13]([C:20]3[CH:21]=[N:22][C:23]([C:26]([F:29])([F:27])[F:28])=[CH:24][CH:25]=3)[C:12]2=[O:30])=[CH:4][CH:3]=1)(=[O:39])[CH3:38]

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 86705196HCID 86705196, compound

Product 1

HCID 86705195HCID 86705195, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

A suspension of N-(6-bromopyridin-3-yl)-2-{(5S)-5-(2-methylpropyl)-2-oxo-3-[6-(trifluoromethyl)pyridin-3-yl]imidazolidin-1-yl}acetamide (78 mg), tributyl(1-ethoxyvinyl)tin (145 mg), bis(triphenylphosphine)palladium(II) dichloride (22 mg), and copper(I) iodide (6.3 mg) in acetonitrile (1.5 mL) was stirred under irradiation with microwave at 150° C. for 2 hr. Saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with chloroform. The organic layer was separated by phase separation cartridge, and the solvent was distilled off under reduced pressure. The residue was purified by preparative HPLC, 1M HCl (1.5 mL) was added to the resulting product, and the mixture was stirred at room temperature for 10 min. The mixture was made basic with saturated sodium hydrogen carbonate, followed by extraction with chloroform, and the solvent was distilled off under reduced pressure to afford the title compound (60 mg).

Workup

  1. extractionfollowed by extraction with chloroform
  2. customThe organic layer was separated by phase separation cartridge
  3. distillationthe solvent was distilled off under reduced pressure
  4. customThe residue was purified by preparative HPLC, 1M HCl (1.5 mL)
  5. additionwas added to the resulting product
  6. stirringthe mixture was stirred at room temperature for 10 min
  7. extractionfollowed by extraction with chloroform
  8. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-38c068f38f4c43938f900e71348c5ea4
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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