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Pyrazolo[1,5-a]pyridine-2-carboxaldehyde, 4,5,6,7-tetrahydro- (9CI) synthesis

6synthesis methods
-

Yield:307313-06-0 77%

Reaction Conditions:

with manganese(IV) oxide in chloroform; for 1 h;Heating / reflux;

Steps:

9.4

Step 4: 4, 5. 6, 7-Tetrahvdronvrazolof1. 5-alpyridine-2-carbaldehyde; Mn02 (activated) (3.36 g) was added to the CHCI3 (44 mL) solution of (4,5, 6, 7-tetrahydropyrazolo [1,5-a] pyridin-2-yl) methanol (673 mg) and refluxed for 1 h under a nitrogen atmosphere. The reaction mixture was filtered through a pad of Celite. The filtrate was reduced under reduced pressure. The residue was applied to silica gel column chromatography, then the column was eluted with n-hexane- AcOEt (2/1-1/2). The titled compound was obtained as pale yellow oil (510 mg, 77%). 'H NMR (CDCI3) 81. 90 (m, 2H), 2.10 (m, 2H), 2.84 (t, 2H, J = 6.4 Hz), 4.23 (t, 2H, J = 6. 2 Hz), 6.52 (s, 1H), 9.92 (s, 1H).

References:

WO2003/93279,2003,A1 Location in patent:Page/Page column 70