Bromosuccinimide → HCID 67994875, compound

HRID 2361413Notes

Reaction equation

HRID 2361413 reaction equation
[Br:1]C1CC(=O)NC1=O.[O:9]=[C:10]1[C:22]2[C:21]3[CH:20]=[CH:19][C:18]([C:23]([O:25][CH3:26])=[O:24])=[CH:17][C:16]=3[NH:15][C:14]=2[CH:13]=[CH:12][NH:11]1>CN(C=O)C>[CH3:26][O:25][C:23]([C:18]1[CH:19]=[CH:20][C:21]2[C:22]3[C:10](=[O:9])[NH:11][CH:12]=[C:13]([Br:1])[C:14]=3[NH:15][C:16]=2[CH:17]=1)=[O:24]

Participants

4

Reactant 2

HCID 38309BromosuccinimideHCID 67995435HCID 67995435, compound

Product 1

HCID 67994875HCID 67994875, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Bromosuccinimide (0.633 g, 3.56 mmol) was quickly added to a stirred mixture of methyl 1-oxo-2,5-dihydro-1H-pyrido[4,3-b]indole-7-carboxylate (0.783 g, 3.23 mmol) in DMF (20 mL) at room temperature. The reaction was exothermic and turned brown. The reaction mixture was stirred for four hours. at room temperature. LC-MS showed complete conversion to the desired product mass. The reaction mixture was poured in to 200 ml water with stirring, then filtered. The residue was washed with water, then slurred in hot methanol, and filtered. The residue was then dried under vacuum overnight to give Methyl-4-bromo-1-oxo-2,5-dihydro-1H-pyrido[4,3-b]indole-7-carboxylate as a light brown solid. [0.898 g, 2.80 mmol, 87% yield]. The product had an HPLC Retention Time=2.703 min [4 min grad, 10% MeOH/water to 90% MeOH/water, 0.1% TFA, YMC COMBISCREEN® ODS-A, 4.6×50 mm, 220 nM]; LC/MS+1 320.86, 322.86

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-029977fa04c84ed8b52a921313904e6f
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

Loading…