Potassium Carbonate → HCID 68842242, compound

HRID 1454819Notes

Reaction equation

HRID 1454819 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[C:10]([CH2:15][C:16](=[O:22])[N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:24](=O)([O-])[O-].[K+].[K+].CB1OB(C)OB(C)O1>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:5][C:6](=[O:23])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH3:24])=[C:10]([CH2:15][C:16](=[O:22])[N:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 68845720HCID 68845720, compound

Product 1

HCID 68842242HCID 68842242, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

(5-Bromo-6-diethylcarbamoylmethyl-pyridin-2-yl)-carbamic acid tert-butyl ester (0.116 g in dioxane (5 mL) was treated successively at RT with potassium carbonate (0.124 g), tetrakis(triphenylphosphine) palladium(0), 35 mg, and trimethylboroxine (38 mg) and then heated to reflux for 22 h. The mixture was cooled to RT, filtered and the filter cake washed with AcOEt. The filtrate was concentrated in vacuo, the residue purified by flash chromatography (heptane/AcOEt 1:1 to 1:4) to give (6-diethylcarbamoylmethyl-5-methyl-pyridin-2-yl)-carbamic acid tert-butyl ester (37 mg) as a colorless gum. MS (ESI): 322.4 (MH+).

Workup

  1. temperatureheated
  2. temperatureto reflux for 22 h
  3. filtrationfiltered
  4. washthe filter cake washed with AcOEt
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue purified by flash chromatography (heptane/AcOEt 1:1 to 1:4)

Sources & evidence

ORD record
ord-a4cfb718bdee413099116f8881abc3f1
Source dataset
uspto-grants-2009_01
Patent number
US07482341B2

Reaction notes

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