Sodium Carbonate → HCID 117877602, compound

HRID 922483Notes

Reaction equation

HRID 922483 reaction equation
[C:1]([O:5][C:6]([N:8]([CH:26]1[CH2:28][CH2:27]1)[CH:9]([C:11]1[CH:12]=[C:13]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:25])[O:23][CH3:24])[C:14](Cl)=[N:15][CH:16]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:29](B1OC(C)(C)C(C)(C)O1)=[CH2:30].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.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>[C:1]([O:5][C:6]([N:8]([CH:26]1[CH2:28][CH2:27]1)[CH:9]([C:11]1[CH:12]=[C:13]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:25])[O:23][CH3:24])[C:14]([CH:29]=[CH2:30])=[N:15][CH:16]=1)[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 117877603HCID 117877603, compound

Product 1

HCID 117877602HCID 117877602, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
85 °C

Procedure

to a solution of methyl [3-(5-{1-[(tert-butoxycarbonyl)(cyclopropyl)amino]ethyl}-2-chloropyridin-3-yl)propyl]carbamate (380 mg) in dimethoxyethane (8 mL) were added vinyl boronic acid pinacol ester (235 μL), 2M sodium carbonate (1.38 mL) and dichlorobis(triphenylphosphine)palladium (II) (65 mg), and the mixture was stirred at 85° C. for 17 hours. The reaction solution was cooled, and then an insoluble was filtered off through Celite, and to the filtrate was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1→1/4) to give methyl [3-(5-{1-[(tert-butoxycarbonyl)(cyclopropyl)amino]ethyl}-2-vinylpyridin-3-yl)propyl]carbamate [REx(113-6)] (282 mg) as a pale yellow oil.

Workup

  1. temperatureThe reaction solution was cooled
  2. filtrationan insoluble was filtered off through Celite
  3. additionto the filtrate was added water
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated saline
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/1→1/4)

Sources & evidence

ORD record
ord-a15c32beb3c54e91913653867baa0fca
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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