Dimethylformamide → 3-ISOPROPYL-[1,2,4]TRIAZOLO[4,3-A]PYRIDINE-6-CARBALDEHYDE

HRID 2121629Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH:11]([CH3:13])[CH3:12])=[N:9][N:10]=2)[CH:7]=1.C([Mg]Cl)(C)C.CN(C)[CH:21]=[O:22]>O1CCCC1>[CH:11]([C:8]1[N:6]2[CH:7]=[C:2]([CH:21]=[O:22])[CH:3]=[CH:4][C:5]2=[N:10][N:9]=1)([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred, cold (0° C.), dark brown solution of 0.48 g of 6-bromo-3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine in 5 mL of tetrahydrofuran was added slowly 1.3 mL of 2 M isopropylmagnesium chloride in tetrahydrofuran. After 30 minutes N,N-dimethylformamide was added; the ice bath was removed, and the mixture was heated to 50° C. for 150 minutes. The mixture was cooled to 22° C., diluted with 1 M hydrochloric acid, and stirred for 10 minutes. The mixture was made basic with saturated aqueous sodium carbonate, and extracted with ethyl acetate (3×). The combined extracts were washed with brine (2×), dried (sodium sulfate), filtered, and the filtrate was concentrated to give a light yellow solid which was crystallized (ethyl acetate, hexanes, and methanol) to give 0.19 g of 3-isopropyl-[1,2,4]triazolo[4,3-a]pyridine-6-carbaldehyde as a faint yellow solid.

Workup

customthe ice bath was removed
temperatureThe mixture was cooled to 22° C.
additiondiluted with 1 M hydrochloric acid
extractionextracted with ethyl acetate (3×)
washThe combined extracts were washed with brine (2×)
dry with materialdried (sodium sulfate)
filtrationfiltered
concentrationthe filtrate was concentrated
customto give a light yellow solid which
customwas crystallized (ethyl acetate, hexanes, and methanol)

Sources & evidence

ORD record: ord-85ac7416e71c46498ac8bcea6e9996c7
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696464B2

Reaction notes

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