Ammonium Chloride → HCID 178487588, compound

Temperature

0 °C

A mixture of 6-methoxy-1H-indazole-3-carboxylic acid (0.200 g, 1.04 mmol) in THF (15 mL) was stirred for 10 min at 0° C. under N2. LAH was added and the mixture was stirred overnight at room temperature under N2. Then, an aqueous NH4Cl solution (5 mL) was added and the reaction mixture was concentrated to half its volume and extracted with EtOAc. The organic layer was washed with brine and water, dried over anhydrous MgSO4, and the solvent removed in vacuo to give a residue. MnO2 (0.680 g, 7.8 mmol) was added to the residue in anhydrous CH2Cl2 (15 mL) at 0° C. with stirring. After the addition, the mixture was stirred at room temperature for 8 h. The mixture was diluted with anhydrous ether (50 mL) and filtered through a pad of Celite. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography to give 6-methoxy-1H-indazole-3-carbaldehyde (0.100 g, 56%).

1. stirringthe mixture was stirred overnight at room temperature under N2
2. concentrationthe reaction mixture was concentrated to half its volume
3. extractionextracted with EtOAc
4. washThe organic layer was washed with brine and water
5. dry with materialdried over anhydrous MgSO4
6. customthe solvent removed in vacuo
7. customto give a residue
8. stirringwith stirring
9. additionAfter the addition
10. stirringthe mixture was stirred at room temperature for 8 h
11. filtrationfiltered through a pad of Celite
12. concentrationThe filtrate was concentrated in vacuo
13. customthe residue was purified by flash chromatography

ORD record

ord-67b624a96b9243deaf6aab606868e5ad

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07456289B2