Diisobutylaluminum hydride → HCID 86664346, compound

HRID 1909021Notes

Reaction equation

HRID 1909021 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]([CH:18]=[CH:19][N:20]=1)[C:12](N(OC)C)=[O:13].CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[CH:10]=[C:11]([CH:12]=[O:13])[CH:18]=[CH:19][N:20]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86664347HCID 86664347, compound

Product 1

HCID 86664346HCID 86664346, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of (2-(2,6-difluoro-phenyl)-N-methoxy-N-methyl-isonicotinamide (Example 33) (268 mg, 0.963 mmol) in toluene (1.2 mL) at −78° C. was added DIBAL (1M in toluene; 1.01 mL, 1.01 mmol) dropwise. The mixture was stirred −78° C. for 2 hours then warmed to 0° C. and the reaction was quenched by the addition of 1M aqueous HCl. The mixture was neutralized using saturated aqueous NaHCO3 solution and then extracted into CHCl3 (×3). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo. The product was purified by SiO2 chromatography providing the title compound (127 mg).

Workup

  1. temperaturethen warmed to 0° C.
  2. customthe reaction was quenched by the addition of 1M aqueous HCl
  3. extractionextracted into CHCl3 (×3)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-8fad6a1166b04c3ab9094be6c3a071d2
Source dataset
uspto-grants-2013_12
Patent number
US08598217B2

Reaction notes

Loading…