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

HRID 706701Notes

Reaction equation

HRID 706701 reaction equation
C(N=C(N(C)C)N(C)C)(C)(C)C.[I:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N+:23]([O-:25])=[O:24])[NH:16][N:15]=1.Br.Br[CH2:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=1>CC#N.O>[I:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[N+:23]([O-:25])=[O:24])[N:16]([CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)[N:15]=1

Participants

6

Reactant 3

HCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 129138592-(2-Bromoethyl)pyridine hydrobromideHCID 178526562HCID 178526562, compound

Product 1

HCID 679763233-iodo-4-nitro-1-(2-(pyridin-2-yl)ethyl)-1H-indazoleYield 34%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

2-Tert-butyl-1,1,3,3-tetramethyl-guanidine (0.48 mL, 2.4 mmol) was added to a mixture of 3-iodo-4-nitro-1H-indazole (0.30 g, 1.0 mmol) and 2-(2-bromoethyl)pyridine hydrobromide (0.30 g, 1.1 mmol) in CH3CN (4 mL). The mixture was stirred at ambient temperature overnight, diluted with H2O (35 mL), stirred for 30 minutes, and then extracted with CHCl3. The combined organic extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel chromatography, eluting with EtOAc, to provide 3-iodo-4-nitro-1-(2-(pyridin-2-yl)ethyl)-1H-indazole (0.14 mg, 34%) as a solid.

Workup

  1. stirringstirred for 30 minutes
  2. extractionextracted with CHCl3
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with EtOAc

Sources & evidence

ORD record
ord-3518179b6d084d8aae756dee8c6b6544
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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