Phosphorus oxychloride → 4-Chloro-6-(pyridin-3-yl)pyrrolo[2,1-f][1,2,4]triazine

HRID 2117119Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[N:14]([CH:15]=2)[N:13]=[CH:12][N:11]=[C:10]3O)[CH:2]=1.O=P(Cl)(Cl)[Cl:19].CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[Cl:19][C:10]1[C:9]2=[CH:8][C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[CH:15][N:14]2[N:13]=[CH:12][N:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a suspension of 6-(pyridin-3-yl)pyrrolo[2,1-f][1,2,4]triazin-4-ol (100 mg, 0.30 mmol) in 10 mL of toluene were added POCl3 (0.18 mL, 1.88 mmol) and DIEA (0.09 mL, 0.5 mmol). The suspension was heated at 100° C. for 7 h. After cooling down, the excess POCl3 was removed under reduced pressure. The residue was suspended in EtOAc, and then neutralized with sat. NaHCO3. The organic layer was then washed with brine and dried over MgSO4. After filtration and concentration, the residue was purified by flash column chromatography to afford the title compound (23 mg, 33%). MS(ESI+) m/z 231.2/233.2 (M+H)+.

Workup

temperatureAfter cooling down
customthe excess POCl3 was removed under reduced pressure
washThe organic layer was then washed with brine
dry with materialdried over MgSO4
filtrationAfter filtration and concentration
customthe residue was purified by flash column chromatography

Sources & evidence

ORD record: ord-81f916129e404f208eaa9f7735b1a200
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439246B2

Reaction notes

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