p-Toluenesulphonyl cyanide → 3-(6-Chloro-1-cyano-7-fluoro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid ethyl ester

HRID 1466946Notes

Reaction equation

HRID 1466946 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11][C:12]2[C:20]3[C:15](=[C:16]([F:22])[C:17]([Cl:21])=[CH:18][CH:19]=3)[NH:14][C:13]=2[CH3:23])[CH:6]=1)[CH3:2].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].S([C:45]#[N:46])(C1C=CC(C)=CC=1)(=O)=O>C1COCC1>[CH2:1]([O:3][C:4](=[O:24])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([S:11][C:12]2[C:20]3[C:15](=[C:16]([F:22])[C:17]([Cl:21])=[CH:18][CH:19]=3)[N:14]([C:45]#[N:46])[C:13]=2[CH3:23])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 87946p-Toluenesulphonyl cyanideHCID 2724254Sodium bis(trimethylsilyl)amideHCID 667655043-(6-Chloro-7-fluoro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid ethyl ester

Product 1

HCID 667656453-(6-Chloro-1-cyano-7-fluoro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-(6-chloro-7-fluoro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid ethyl ester (0.50 g, 1.37 mmol) in THF (10 mL) at RT was added sodium bis(trimethylsilyl)amide (0.76 mL of a 2.0M solution in THF, 1.51 mmol). After 30 minutes, tosyl cyanide (0.279 g, 1.54 mmol) was added, and the reaction was stirred for 2 hrs, then subjected to standard aqueous workup. The crude residue was purified on silica gel (0-30% EtOAc in hexanes) to afford the title compound.

Workup

  1. customThe crude residue was purified on silica gel (0-30% EtOAc in hexanes)

Sources & evidence

ORD record
ord-90e0db6ef92341488f00f15690b55a1a
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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