Diisobutylaluminum hydride → (3-Methylimidazo[2,1-f][1,6]naphthyridin-2-yl)methanol
Reaction equation
[CH3:1][C:2]1[N:14]2[C:5]([C:6]3[CH:7]=[CH:8][CH:9]=[N:10][C:11]=3[CH:12]=[CH:13]2)=[N:4][C:3]=1[C:15](OC)=[O:16].CC(C[AlH]CC(C)C)C.[Cl-].[NH4+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:1][C:2]1[N:14]2[C:5]([C:6]3[CH:7]=[CH:8][CH:9]=[N:10][C:11]=3[CH:12]=[CH:13]2)=[N:4][C:3]=1[CH2:15][OH:16]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of methyl 3-methylimidazo[2,1-f][1,6]naphthyridine-2-carboxylate (100 mg, 0.39 mmol) in DCM (8 mL) was cooled to 0° C. DIBAL-H (1 M in cyclohexane, 1.2 mL, 1.2 mmol) was added dropwise over 10 min. The mixture was stirred at 0° C. for 1 h. 2 mL of saturated ammonium chloride aqueous solution was added slowly to quench the reaction. Then 5 mL of saturated sodium bicarbonate aqueous solution was added. The mixture was extracted with DCM (3×10 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to give the crude product, which was purified by column chromatography to give 42 mg of the product as a yellow solid. ESI MS: m/z 214.1 [M+H]+.
Workup
- customto quench
- customthe reaction
- extractionThe mixture was extracted with DCM (3×10 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- customto give the crude product, which
- customwas purified by column chromatography
Sources & evidence
- ORD record
- ord-715ae4f56898465680d3bf62c10cf60c
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249162B2
Reaction notes
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