Dichloromethane → 6-Bromo-2-(methylsulfanyl)pyrrolo[2,1-f][1,2,4]triazine

HRID 1262279Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[N:8]=[C:7]([S:11][CH3:12])[N:6]=[C:5]2Cl.[BH4-].[Na+].C(Cl)Cl>C(O)(C)C>[Br:1][C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[N:8]=[C:7]([S:11][CH3:12])[N:6]=[CH:5]2

Participants

Conditions

Temperature: 60 °C

Procedure

Into a round bottom flask, 6-Bromo-4-chloro-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (6.00 g, 21.5 mmoles) was suspended in Isopropyl alcohol (69 mL) at 55° C. Sodium borohydride (1.71 g, 0.0452 mol) was added and heated at 60° C. for 3 hours. The reaction was allowed to cool to RT. The solid was filtered and washed with DCM. The solvent was removed under vacuum to a viscous oil. Methylene chloride (100 mL, 2 mol) was added to the viscous oil. Dichlorodicyanoquinone (5.38 g, 0.0237 mol) was then added portion wise over 15 minutes. The mixture was stirred for 30 minutes. The solid was filtered through Celite and washed with DCM. The solvent was removed under vacuum. The reaction was purified via ISCO column chromatography with hexane and EtOAca as eluant (0 to 8% EtOAC). The collected fractions afforded 6-Bromo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine as a light yellow solid (1.46, 27%).

Workup

temperatureto cool to RT
filtrationThe solid was filtered
washwashed with DCM
customThe solvent was removed under vacuum to a viscous oil
filtrationThe solid was filtered through Celite
washwashed with DCM
customThe solvent was removed under vacuum
customThe reaction was purified via ISCO column chromatography with hexane and EtOAca as eluant (0 to 8% EtOAC)

Sources & evidence

ORD record: ord-e5a86cb765854b59b415bf744e1d80d0
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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