Tributylammonium fluoride → 3-ethynyl-5-nitro-1-trityl-1H-indazole

HRID 1038149Notes

Reaction equation

HRID 1038149 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[N:8]=[C:7]2[C:32]#[C:33][Si](C)(C)C)([O-:3])=[O:2].[F-].C([NH+](CCCC)CCCC)CCC>C1COCC1>[C:32]([C:7]1[C:6]2[C:10](=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:9]([C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:8]=1)#[CH:33]

Participants

4

Reactant 2

HCID 11217984Tributylammonium fluorideHCID 576858635-Nitro-3-trimethylsilanylethynyl-1-trityl-1H-indazole

Product 1

HCID 576857343-ethynyl-5-nitro-1-trityl-1H-indazoleYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-nitro-3-trimethylsilanylethynyl-1-trityl-1H-indazole (700 mg, 1.4 mmol) in THF (5 mL) was added tributylammonium fluoride (1M, 2.8 mL, 2.8 mmol). The resulted solution was stirred at room temperature for 2 hours. TLC showed the completion of reaction. After removal the solvent under vacuum, the product was purified using silica (20 hexane in dichloromethane) to give 560 mg of titled product (93% yield).

Workup

  1. customthe completion of reaction
  2. customAfter removal the solvent under vacuum
  3. customthe product was purified

Sources & evidence

ORD record
ord-f35d4d33e69944e49c5c88bb8a35ec27
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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