N,N-Dimethyl-2-nitroethenamine → 4-Bromo-3-(2-nitrovinyl)-1H-indole-7-carboxamide

HRID 2361432Notes

Reaction equation

HRID 2361432 reaction equation
[Br:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([NH2:13])=[O:12])=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.CN(C)/[CH:16]=[CH:17]/[N+:18]([O-:20])=[O:19]>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([NH2:13])=[O:12])=[C:7]2[C:3]=1[C:4]([CH:16]=[CH:17][N+:18]([O-:20])=[O:19])=[CH:5][NH:6]2

Participants

4

Reactant 2

HCID 637928N,N-Dimethyl-2-nitroethenamineHCID 497579964-Bromo-1H-indole-7-carboxamide

Product 1

HCID 679946544-Bromo-3-(2-nitrovinyl)-1H-indole-7-carboxamide

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A dark red-brown solution of 4-bromo-1H-indole-7-carboxamide (0.79 g, 3.30 mmol) and (E)-N,N-dimethyl-2-nitroethenamine (0.422 g, 3.63 mmol) in TFA (9.44 mL) was stirred at room temperature overnight. After 16 h, LCMS indicated residual starting materials in addition to desired product. Additional (E)-N,N-dimethyl-2-nitroethenamine (77 mg) was added and the mixture was stirred at room temperature for 6 h. The mixture was partitioned between 1 M NaOH (pH was adjusted to ca. 4) and EtOAc. The organic phase was washed with NaHCO3 (aq) and brine, dried and concentrated to afford a bright orange-red solid. The crude product was suspended in EtOAc and the desired product was collected by filtration, washed with EtOAc and air dried to provide a solid (0.89 g, 87% yield). LCMS (M+H)+ m/z 309.7, 311.7.

Sources & evidence

ORD record
ord-0b47d584697142ae80d8442d3adf2b48
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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