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

HRID 2275189Notes

Reaction equation

HRID 2275189 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-146a377a67f047f7bee843d00592d4e0
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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