N-bromobutanimide → Ethyl 4-amino-7-bromo-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

HRID 73672Notes

Reaction equation

[NH2:1][C:2]1[C:7]2=[C:8]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.[Br:25]N1C(=O)CCC1=O>C(#N)C>[NH2:1][C:2]1[C:7]2=[C:8]([C:16]3[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=3)[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:10]([Br:25])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Ethyl 4-amino-5-(4-nitrophenyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (2.0 g, 6.11 mmol) was suspended in ACN and treated with N-bromosuccinimide (1.20 g, 6.72 mmol). The dark suspension was heated to 60° C. for 1 h. The suspension was cooled and filtered. The brown solid was washed with ACN and MeOH. The product was collected by filtration to give 2.06 g of a yellow brown solid (83%). 1H-NMR (DMSO-d6) δ 8.26 (d, J=8.8, 2H), 8.07 (s, 1H), 7.64 (d, J=8.8, 2H), 4.02 (q, J=7.0, 2H), 0.95 (t, J=7.0, 3H); MS [M+H]+=406.1, 408.0; LCMS RT=2.93.

Workup

temperatureThe suspension was cooled
filtrationfiltered
washThe brown solid was washed with ACN and MeOH
filtrationThe product was collected by filtration

Sources & evidence

ORD record: ord-b433018b5b37496199947196d20a5637
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829185B2

Reaction notes

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