Diisobutylaluminum hydride → HCID 58318628, compound

HRID 473436Notes

Reaction equation

HRID 473436 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:20]([C:21]([O:23]C)=O)=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][N:17]=2)[N:12]=1)(=[O:4])=[O:3].[CH3:25]C(C[AlH]CC(C)C)C>C(Cl)Cl>[CH3:25][CH:21]([C:20]1[C:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[S:2]([CH3:1])(=[O:4])=[O:3])=[N:12][C:13]2[C:18]([CH:19]=1)=[N:17][CH:16]=[CH:15][CH:14]=2)[OH:23]

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 67240037Methyl 2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridine-3-carboxylate

Product 1

HCID 58318628HCID 58318628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridine-3-carboxylate (1.2 g, 3.5 mmol) in DCM (30 mL) was added DIBAL-H (35 mL, 35 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 (2-(2-(methylsulfonyl)phenyl)-1,5-naphthyridin-3-yl)methanol: LC-MS (ESI) m/z 315.0 [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-010bb74092a64f3a8fcfeee1ca0aafc9
Source dataset
uspto-grants-2014_01
Patent number
US08633313B2

Reaction notes

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