Water → HCID 67396611, compound

HRID 1426686Notes

Reaction equation

HRID 1426686 reaction equation
[F:1][C:2]1[C:7]([C:8]2[NH:12][CH:11]=[C:10]([C:13](OCC)=[O:14])[C:9]=2[CH3:18])=[CH:6][CH:5]=[CH:4][N:3]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.O>O1CCCC1>[F:1][C:2]1[C:7]([C:8]2[NH:12][CH:11]=[C:10]([CH2:13][OH:14])[C:9]=2[CH3:18])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 21225700DiisobutylaluminumhydrideHCID 67395699HCID 67395699, compound

Product 1

HCID 67396611HCID 67396611, compoundYield 41.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of ethyl 5-(2-fluoropyridin-3-yl)-4-methyl-1H-pyrrole-3-carboxylate (5.01 g) in tetrahydrofuran (50 mL) was cooled to −78° C., a 1.5 mol/L toluene solution (45 mL) of diisobutylaluminum hydride was added dropwise, and the mixture was stirred at 0° C. for 1 hr. Water was added to the reaction mixture, insoluble materials were filtered off, and the filtrate was extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title compound as colorless crystals (yield 1.72 g, 41%).

Workup

  1. filtrationwere filtered off
  2. extractionthe filtrate was extracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-a79b489b544741278e195cc588148819
Source dataset
uspto-grants-2015_01
Patent number
US08933105B2

Reaction notes

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