Phosphorus oxychloride → 7-bromo-N-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-amine

HRID 643680Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][NH:9][C:10]([NH:12][CH:13]([CH3:15])[CH3:14])=O)[CH:3]=1.P(Cl)(Cl)(Cl)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])=[N:9][N:8]=[C:4]2[CH:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A heterogeneous mixture of 1-(4-bromopyridin-2-yl)-4-isopropylsemicarbazide (0.315 g, 1.15 mmol) in phosphorous oxychloride (1.06 mL, 11.5 mmol) was heated at 100° C. for 2 h. The homogenous solution was allowed to cool to RT. Toluene (10 mL) was added and removed in vacuo (3×). DCM (20 mL) and saturated sodium bicarbonate (aq.) was added to the solid and stirred. The off-white solid was collected by filtration and washed with DCM to give 7-bromo-N-isopropyl-[1,2,4]triazolo[4,3-a]pyridin-3-amine. MS (ESI, pos. ion) m/z: 255.2 (M+1).

Workup

temperatureto cool to RT
customremoved in vacuo (3×)
additionDCM (20 mL) and saturated sodium bicarbonate (aq.) was added to the solid
filtrationThe off-white solid was collected by filtration
washwashed with DCM

Sources & evidence

ORD record: ord-745d51617c594e6ab4cbe68bc1a21228
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700593B2

Reaction notes

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