Reaction #90091

ord-3ff0c68ac71a4ed383672c34660ff6b8

Reaction equation

CS(=O)(=O)O.O=P12OP3(=O)OP(=O)(O1)OP(=O)(O2)O3
Phosphorus pentoxide methanesulfonic acid
CCOC(=O)c1c(C(C)(C)c2ccc(OC)c(Br)c2)[nH]c2cc(C#N)ccc12
2-[1-(3-bromo-4-methoxy-phenyl)-1-methyl-ethyl]-6-cyano-1H-indole-3-carboxylic acid ethyl ester
O
water
COc1cc2c(cc1Br)C(C)(C)c1[nH]c3cc(C#N)ccc3c1C2=O
title compound
Yield 85.0%
COc1cc2c(cc1Br)C(C)(C)c1[nH]c3cc(C#N)ccc3c1C2=O
8-Bromo-9-methoxy-6,6-dimethyl-11-oxo-6,11-dihydro-5H-benzo[b]carbazole-3-carbonitrile
Yield 85.0%

Solvents

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Filtrationthe precipitated solid was filtered

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%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09440922B2uspto-grants-2016_09