Ethynylpyridine → 6-Nitro-3-pyridin-2-ylethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole

HRID 1827477Notes

Reaction equation

HRID 1827477 reaction equation
I[C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[N:3]=1.[C:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1)#[CH:23]>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.C(N(CC)CC)C>[N+:11]([C:7]1[CH:6]=[C:5]2[C:10]([C:2]([C:23]#[C:22][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=3)=[N:3][N:4]2[CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])=[CH:9][CH:8]=1)([O-:13])=[O:12]

Participants

5

Reactant 2

HCID 137268EthynylpyridineHCID 218774881H-Indazole, 3-iodo-6-nitro-1-[[2-(trimethylsilyl)ethoxy]methyl]-

Product 1

HCID 235778736-Nitro-3-pyridin-2-ylethynyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 8471TriethylamineSolvent

Procedure

A mixture of 3-Iodo-6-nitro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazole (838 mg, 2.0 mmol), 2-ethynyl-pyridine (242 μL, 2.4 mmol), and triethylamine (6.0 mL), were degassed and flushed with argon, then treated with Cul (8 mg, 0.042 mmol), and Pd(PPh3)2Cl2 (16 mg, 0.023 mmol). The resulting mixture was stirred overnight at room temperature, at which time HPLC indicated all starting material had been consumed. The mixture was purified by stripping of volatiles under high vacuum, then passing through a plug of silica eluted with ethyl acetate. The resulting product was used in the next step without further purification. ESIMS (M+H+): 395.1.

Workup

  1. customwere degassed
  2. customflushed with argon
  3. customhad been consumed
  4. customThe mixture was purified
  5. washeluted with ethyl acetate
  6. customThe resulting product was used in the next step without further purification

Sources & evidence

ORD record
ord-0e45ef5a33984982878ff409b51b1734
Source dataset
uspto-grants-2006_05
Patent number
US07053107B2

Reaction notes

Loading…