Water → 6-Chloro-4-(1H-indol-2-yl)-2H-pyridazin-3-one

HRID 2234127Notes

Reaction equation

HRID 2234127 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]1[CH:22]=[C:21]([Cl:23])[N:20]=[N:19][C:18]=1[O:24]C)=O)(C)(C)C.C[Si](Cl)(C)C.O>C(#N)C>[Cl:23][C:21]1[CH:22]=[C:17]([C:9]2[NH:8][C:16]3[C:11]([CH:10]=2)=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:18](=[O:24])[NH:19][N:20]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 866120482-(6-Chloro-3-methoxy-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 1359618866-Chloro-4-(1H-indol-2-yl)-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2 g of 2-(6-chloro-3-methoxy-pyridazin-4-yl)-indole-1-carboxylic acid tert-butyl ester is treated for 16 h at 85° C. with 2.76 g of KI and 1.8 g of trimethylsilylchloride in 200 ml acetonitrile. On completion of the reaction the reaction solution is poured into water and the precipitated product is isolated by filtration. Yield: 1.33 g. LC-MS (ES+) 246 (M+H)+.

Workup

  1. customOn completion of the reaction the reaction solution
  2. customthe precipitated product is isolated by filtration

Sources & evidence

ORD record
ord-0c27febd4b234755a93476f8fe43ac2d
Source dataset
uspto-grants-2010_05
Patent number
US07709466B2

Reaction notes

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