6-iodo-1H-indazole → HCID 68444957, compound

HRID 1163405Notes

Reaction equation

HRID 1163405 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=1)#[CH:2].I[C:14]1[CH:22]=[C:21]2[C:17]([CH:18]=[N:19][NH:20]2)=[CH:16][CH:15]=1>C1COCC1.C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]Cl>[NH:20]1[C:21]2[C:17](=[CH:16][CH:15]=[C:14]([C:2]#[C:1][C:3]3[CH:8]=[CH:7][C:6]([NH2:9])=[C:5]([N+:10]([O-:12])=[O:11])[CH:4]=3)[CH:22]=2)[CH:18]=[N:19]1

Participants

7

Reactant 2

HCID 129912416-iodo-1H-indazoleHCID 50998788HCID 50998788, compound

Product 1

HCID 68444957HCID 68444957, compoundYield 35%

Reagents, catalysts & solvents 4

HCID 62652Cuprous chlorideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 4-ethynyl-2-nitro-phenylamine (1.306 g, 8.05 mmol), 6-iodo-1H-indazole (1.965 g, 8.05 mmol), dichlorobis(triphenylphosphine)palladium(II) (122 mg, 0.24 mmol) and copper(I) chloride (54.4 mg, 0.28 mmol) in THF (8 mL) and triethyl amine (8 mL) was stirred at room temperature overnight. Purification by column chromatography on silica gel gave 4-(1H-indazol-6-ylethynyl)-2-nitrophenylamine as red solid (777 mg, 2.79 mmol, yield 35%). LC-MS m/z: 279 (M+1)+.

Workup

  1. customPurification by column chromatography on silica gel

Sources & evidence

ORD record
ord-1846b39246cc47a0aecc141cc1bd5374
Source dataset
uspto-grants-2010_10
Patent number
US07820821B2

Reaction notes

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