Water → HCID 66924956, compound

HRID 554241Notes

Reaction equation

HRID 554241 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:11][CH:10]=[C:9]([C:12](OCC)=[O:13])[CH:8]=1.[H-].C([Al+]CC(C)C)C(C)C.O.S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.C1(C)C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:11][CH:10]=[C:9]([CH2:12][OH:13])[CH:8]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21225700DiisobutylaluminumhydrideHCID 66924741HCID 66924741, compound

Product 1

HCID 66924956HCID 66924956, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution (30 mL) of ethyl 5-(pyridin-2-yl)-1H-pyrrole-3-carboxylate (1.62 g) in tetrahydrofuran was cooled to −50° C., and a 1.5 mol/L solution (15 mL) of diisobutylaluminum hydride in toluene was added dropwise by small portions. The mixture was further stirred at 0° C. for 1 hr, water (3 mL) was added to the reaction mixture and the mixture was stirred at room temperature for 1 hr. Celite and anhydrous magnesium sulfate were added and the mixture was further stirred for 15 min and filtrated. The obtained filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→1:3) to give the title compound as colorless crystals (yield 1.15 g, 88%).

Workup

  1. stirringthe mixture was stirred at room temperature for 1 hr
  2. stirringthe mixture was further stirred for 15 min
  3. filtrationfiltrated
  4. concentrationThe obtained filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=1:1→1:3)

Sources & evidence

ORD record
ord-484845b328664b5482792a58528b1fd8
Source dataset
uspto-grants-2011_11
Patent number
US08048909B2

Reaction notes

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