N-Iodosuccinimide → 5-Chloro-7-iodo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

HRID 1262428Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][N:5]2[C:10]=1[CH:9]=[N:8][C:7]([S:11][CH3:12])=[N:6]2.[I:13]N1C(=O)CCC1=O>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([I:13])[N:5]2[C:10]=1[CH:9]=[N:8][C:7]([S:11][CH3:12])=[N:6]2

Participants

Conditions

Temperature: 60 °C

Procedure

5-Chloro-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (54 mg, 0.27 mmol) was dissolved in 1,2-Dichloroethane (2.0 mL and then N-Iodosuccinimide (75 mg, 0.33 mmol) was added in one portion and the reaction was stirred in a vial at 60° C. overnight. The heterogenous mixture was powdered onto silica gel (0.75 g) and purified on ISCO (12 g, 0-5% EtOAc:Hex) to afford 5-Chloro-7-iodo-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (49 mg; Yield=56%) as a yellow solid. m.p. 216-220° C.; LCMS (Bruker, Fragile): 4.0 min, m/z=326; 1H-NMR (CDCl3): 8.55 (s, 1H), 6.90 (s, 1H), 2.63 (s, 3H).

Workup

custompurified on ISCO (12 g, 0-5% EtOAc:Hex)

Sources & evidence

ORD record: ord-896db0daa651471899dd8b664e39c5cd
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08471005B2

Reaction notes

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