Diisobutylaluminum hydride → HCID 58318610, compound

HRID 473428Notes

Reaction equation

HRID 473428 reaction equation
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([C:22]([O-])=[O:23])[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[S:18]([CH3:21])(=[O:20])=[O:19])=[N:9]2)=[N:4][CH:3]=1.[CH3:25]C(C[AlH]CC(C)C)C>C(Cl)Cl>[CH3:25][CH:22]([C:7]1[C:8]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[S:18]([CH3:21])(=[O:20])=[O:19])=[N:9][C:10]2[C:5]([CH:6]=1)=[N:4][CH:3]=[C:2]([F:1])[CH:11]=2)[OH:23]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 86654699HCID 86654699, compound

Product 1

HCID 58318610HCID 58318610, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-fluoro-2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridine-3-carboxylate (1.2 g, 3.33 mmol) in DCM (27 mL) was added DIBAL-H (34 mL, 33.3 mmol) at −78° C. The reaction mixture was stirred for 4 h at same temperature. The reaction mixture was quenched with satd solution of ammonium chloride and extracted with EtOAc. The organic layer was concentrated in vacuo to give methyl (7-fluoro-2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)methanol: LC-MS (ESI) m/z 333.1 [M+H]+. It was carried on crude for next step.

Workup

  1. customThe reaction mixture was quenched with satd solution of ammonium chloride
  2. extractionextracted with EtOAc
  3. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-f0c5c74926f34a07b91ff0c929dedf16
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

Loading…