2-tert-Butyl-1,1,3,3-tetramethylguanidine → 3-iodo-4-nitro-1-((5-(trifluoromethyl)pyridin-2-yl)methyl)-1H-indazole

HRID 706694Notes

Reaction equation

HRID 706694 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.C(N=C(N(C)C)N(C)C)(C)(C)C.Cl.Cl[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][N:30]=1>CC#N>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:37])([F:36])[F:38])=[CH:31][N:30]=2)[N:3]=1

Participants

5

Reactant 3

HCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 686914462-(Chloromethyl)-5-(trifluoromethyl)pyridine hydrochlorideHCID 178526562HCID 178526562, compound

Product 1

HCID 866993433-iodo-4-nitro-1-((5-(trifluoromethyl)pyridin-2-yl)methyl)-1H-indazoleYield 54.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a round bottom flask was added 3-iodo-4-nitro-1H-indazole (0.580 g, 2.01 mmol) and CH3CN (10 mL). 2-tert-Butyl-1,1,3,3-tetramethylguanidine (0.890 mL, 4.41 mmol) was added and the mixture was stirred for 5 minutes. 2-(Chloromethyl)-5-(trifluoromethyl)pyridine hydrochloride (0.512 g, 2.21 mmol) was added as a CH3CN solution (4 mL) and the mixture was stirred at ambient temperature overnight. The mixture was concentrated and diluted with saturated aqueous NH4Cl (20 mL) and EtOAc (60 mL). The layers were mixed and separated and the organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The crude product was purified by column chromatography (50% EtOAc/hexane) to provide 0.490 g (54%) of the product as an orange solid.

Workup

  1. stirringthe mixture was stirred at ambient temperature overnight
  2. concentrationThe mixture was concentrated
  3. additiondiluted with saturated aqueous NH4Cl (20 mL) and EtOAc (60 mL)
  4. additionThe layers were mixed
  5. customseparated
  6. washthe organic phase was washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified by column chromatography (50% EtOAc/hexane)

Sources & evidence

ORD record
ord-04b77aa03b2047219e241bcf66824f10
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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