Toluene → HCID 89649425, compound

HRID 2207653Notes

Reaction equation

HRID 2207653 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:23])=[C:8]([C:10]2[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[N:13]=[C:12]([C:19](OC)=[O:20])[CH:11]=2)[CH:9]=1)[CH3:2].CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]([F:23])=[C:8]([C:10]2[CH:15]=[C:14]([CH:16]([CH3:17])[CH3:18])[N:13]=[C:12]([CH:19]=[O:20])[CH:11]=2)[CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 89649130HCID 89649130, compound

Product 1

HCID 89649425HCID 89649425, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of methyl 4-(5-ethoxy-2-fluoro-phenyl)-6-isopropyl-pyridine-2-carboxylate (which may be prepared as described in Description 115) (0.72 g, 2.27 mmol) in THF (20 mL) was cooled to −78° C. under nitrogen and was treated dropwise with 1M DIBAL in toluene (4.54 mL, 4.54 mmol) over 10 minutes. The mixture was stirred at −78° C. for 2 hrs. The mixture was quenched with satd. aq. NH4Cl solution (5 ml) and the mixture was allowed to reach room temperature and stirred for 30 mins. Celite was added to the mixture and the mixture was stirred for 10 minutes and then filtered through Celite and concentrated to give 4-(5-ethoxy-2-fluoro-phenyl)-6-isopropyl-pyridine-2-carbaldehyde (D116) (0.57 g);

Workup

  1. customThe mixture was quenched with satd
  2. customto reach room temperature
  3. stirringstirred for 30 mins
  4. additionCelite was added to the mixture
  5. stirringthe mixture was stirred for 10 minutes
  6. filtrationfiltered through Celite
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4b040b9a37c84d7d8dcbff9529ec0577
Source dataset
uspto-grants-2016_06
Patent number
US09376436B2

Reaction notes

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