Pyrrole → tert-butyl(5-(1H-pyrrol-1-yl)pyridin-3-yl)carbamate

HRID 340457Notes

Reaction equation

HRID 340457 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[CH:11]=[CH:10][CH:9]=[CH:8]1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[C:54]([O:58][C:59](=[O:68])[NH:60][C:61]1[CH:62]=[N:63][CH:64]=[C:65](Br)[CH:66]=1)([CH3:57])([CH3:56])[CH3:55]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O.O1CCOCC1>[C:54]([O:58][C:59](=[O:68])[NH:60][C:61]1[CH:62]=[N:63][CH:64]=[C:65]([N:7]2[CH:11]=[CH:10][CH:9]=[CH:8]2)[CH:66]=1)([CH3:57])([CH3:55])[CH3:56]

Participants

8

Reactant 4

HCID 8027PyrroleHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 11403050tert-Butyl (5-bromopyridin-3-yl)carbamate

Product 1

HCID 89546780tert-butyl(5-(1H-pyrrol-1-yl)pyridin-3-yl)carbamateYield 37.9%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Cesium carbonate (214 mg), pyrrole (30 mg), Xantphos (63 mg), and Pd2(dba)3 (50 mg) were added to a 1,4-dioxane solution (5 mL) containing tert-butyl(5-bromopyridin-3-yl)carbamate (100 mg) in a nitrogen atmosphere, followed by stirring at 100° C. for 8 hours. The reaction solution was adjusted to room temperature, and water was added, followed by extraction with ethyl acetate. The organic layer was washed with saturated saline and dried over anhydrous sodium sulfate. Then, the solvent was distilled away under reduced pressure, the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=5:1 to 1:1), and a light yellow solid of tert-butyl(5-(1H-pyrrol-1-yl)pyridin-3-yl)carbamate (36 mg) was thus obtained.

Workup

  1. customwas adjusted to room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, the solvent was distilled away under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=5:1 to 1:1)

Sources & evidence

ORD record
ord-9eb721a51edf45dd9cffea111cbcb4e5
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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