Water → HCID 67353847, compound

HRID 1846148Notes

Reaction equation

HRID 1846148 reaction equation
[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[C:12]([CH3:14])[C:11](Br)=[C:10]([CH3:16])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[OH-:17].[K+].O>O1CCOCC1.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]>[CH3:1][C:2]1[N:3]([C:8]2[CH:13]=[C:12]([CH3:14])[C:11]([OH:17])=[C:10]([CH3:16])[N:9]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 67354691HCID 67354691, compound

Product 1

HCID 67353847HCID 67353847, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
100 °C

Procedure

To a stirred solution containing 2.37 g (8.49 mmol) of 2-(2,5-dimethyl-1H-pyrrol-1-yl)-5-bromo-4,6-dimethylpyridine (14) in 30 mL of dioxane-degassed water 1:1 were added 311 mg (0.34 mmol) of Pd2dba3 followed by 288 mg (0.68 mmol) of 2-Di-tert-butylphosphino-2′,4′,6′-triisopropylbyphenyl (L1) and 1.42 g (25.46 mmol) of potassium hydroxide. The reaction mixture was stirred at 100° C. under argon atmosphere during 3 h. The reaction mixture was poured into 150 mL of water and extracted with two portions of 150 mL of ethyl acetate. The combined organic solution was washed with a portion of 100 mL of brine, dried (MgSO4) and the concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column. Elution with hexanes-ethyl acetate 3:1 gave the expected product as a white solid: yield 1.19 g (65%). 1H-NMR (CDCl3) δ 6.89 (s, 1H), 5.75 (s, 2H), 2.45 (s, 3H), 2.22 (s, 3H), 2.05 (s, 6H); 13C-NMR (CDCl3) δ 148.80, 145.03, 143.12, 135.51, 128.43, 122.32, 106.01, 18.48, 15.95, 12.80.

Workup

  1. customdegassed water 1:1
  2. extractionextracted with two portions of 150 mL of ethyl acetate
  3. washThe combined organic solution was washed with a portion of 100 mL of brine
  4. dry with materialdried (MgSO4)
  5. concentrationthe concentrated under diminished pressure
  6. customThe residue was purified by chromatography on a silica gel column
  7. washElution with hexanes-ethyl acetate 3:1

Sources & evidence

ORD record
ord-f75e8b168b6241d7a5cd9d2a43459978
Source dataset
uspto-grants-2015_02
Patent number
US08952025B2

Reaction notes

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