Hydrogen Bromide → 7-amino-4-bromo-9H-carbazole-1-carboxamide hydrobromide

HRID 1811155Notes

Reaction equation

HRID 1811155 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15](=[O:17])[NH2:16])=[C:11]2[C:3]=1[C:4]1[CH:5]=[CH:6][C:7]([NH:18]C(=O)OCC3C=CC=CC=3)=[CH:8][C:9]=1[NH:10]2.Br>CCOCC>[BrH:1].[NH2:18][C:7]1[CH:8]=[C:9]2[C:4]([C:3]3[C:2]([Br:1])=[CH:14][CH:13]=[C:12]([C:15]([NH2:16])=[O:17])[C:11]=3[NH:10]2)=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 66606174benzyl 5-bromo-8-carbamoyl-9H-carbazol-2-ylcarbamate

Product 1

HCID 666057197-amino-4-bromo-9H-carbazole-1-carboxamide hydrobromide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of benzyl 5-bromo-8-carbamoyl-9H-carbazol-2-ylcarbamate (Example 50-3, 2.18 g, 4.97 mmol) in hydrogen bromide (30-35% in acetic acid, 11.9 mL, 59.7 mmol) was stirred at rt for 30 min. The mixture was diluted with ether (100 mL) and the precipitate was collected by filtration, washed with ether and dried to provide 7-amino-4-bromo-9H-carbazole-1-carboxamide, hydrobromide salt, as a light yellow solid (2.20 g). 1H NMR (400 MHz, DMSO-d6) δ 12.02 (1 H, s), 8.69 (1 H, d, J=8.5 Hz), 8.28 (1 H, br. s.), 7.91 (1 H, d, J=8.0 Hz), 7.84 (1 H, d, J=1.8 Hz), 7.65 (1H, br. s.), 7.51 (1 H, d, J=8.3 Hz), 7.25 (1 H, dd, J=8.4, 1.9 Hz). Mass spectrum m/z 304, 306 (M+H)+. The salt was partitioned between EtOAc and NaHCO3 (aq). Residual solid was collected by filtration, washed with EtOAc and water and dried. The organic phase of the filtrate was separated, washed with brine, and dried and concentrated. The solid residue was combined with the filtered solid, dissolved in acetone, filtered to remove undissolved solid, and the filtrate was concentrated to provide 7-amino-4-bromo-9H-carbazole-1-carboxamide, hydrobromide salt, as a light yellow solid (1.62 g, 96%).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with ether
  3. customdried

Sources & evidence

ORD record
ord-e46dfa210ae84d3b82bd774ea0adaee9
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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