Water → 8-Bromo-9-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile

HRID 61813Notes

Reaction equation

HRID 61813 reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CS(O)(=O)=O.C(O[C:23]([C:25]1[C:33]2[C:28](=[CH:29][C:30]([C:34]#[N:35])=[CH:31][CH:32]=2)[NH:27][C:26]=1[C:36]([C:39]1[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[C:41]([Br:47])[CH:40]=1)([CH3:38])[CH3:37])=[O:24])C.O>CC#N>[Br:47][C:41]1[C:42]([O:45][CH3:46])=[CH:43][C:44]2[C:23](=[O:24])[C:25]3[C:33]4[C:28](=[CH:29][C:30]([C:34]#[N:35])=[CH:31][CH:32]=4)[NH:27][C:26]=3[C:36]([CH3:38])([CH3:37])[C:39]=2[CH:40]=1

Participants

5

Reactant 3

HCID 962WaterHCID 668341792-[1-(3-bromo-4-methoxy-phenyl)-1-methyl-ethyl]-6-cyano-1H-indole-3-carboxylic acid ethyl esterHCID 86584057Phosphorus Pentoxide-Methanesulfonic Acid

Product 1

HCID 668340788-Bromo-9-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrileYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Phosphorus pentoxide-methanesulfonic acid (12 mL) was added with 2-[1-(3-bromo-4-methoxy-phenyl)-1-methyl-ethyl]-6-cyano-1H-indole-3-carboxylic acid ethyl ester (Compound K5, 1.0 g, 2.27 mmol), and the mixture was stirred at room temperature for 20 min. The reaction solution was diluted with MeCN (20 mL), poured into water (20 mL), and the precipitated solid was filtered to obtain the title compound (yellow solid, 763 mg, 85%).

Workup

  1. filtrationthe precipitated solid was filtered

Sources & evidence

ORD record
ord-3ff0c68ac71a4ed383672c34660ff6b8
Source dataset
uspto-grants-2016_09
Patent number
US09440922B2

Reaction notes

Loading…