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

HRID 706690Notes

Reaction equation

HRID 706690 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.Br.BrC[C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[C:23](N=C(N(C)C)N(C)C)(C)(C)C>CC#N.O>[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]([CH2:23][C:22]2[CH:21]=[N:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1

Participants

6

Reactant 3

HCID 35715812-tert-Butyl-1,1,3,3-tetramethylguanidineHCID 127522194-(Bromomethyl)pyridine hbrHCID 178526562HCID 178526562, compound

Product 1

HCID 866993413-iodo-4-nitro-1-(pyridin-3-ylmethyl)-1H-indazoleYield 76.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a flask was added 3-iodo-4-nitro-1H-indazole (0.300 g, 1.04 mmol) and 4-(bromomethyl)pyridine hydrobromide (0.315 g, 1.25 mmol) which were slurried in CH3CN (5.0 mL). 2-tert-Butyl-1,1,3,3-tetramethylguanidine (0.460 mL, 2.28 mmol) was added and the mixture was stirred overnight. The mixture was diluted with water (20 mL) and stirred for 15 minutes and filtered. The collected solids were washed with water followed by Et2O and hexanes, and dried under vacuum to provide the title compound as a brown powder (0.304 g, 71%), which was used directly in the subsequent step.

Workup

  1. stirringstirred for 15 minutes
  2. filtrationfiltered
  3. washThe collected solids were washed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-2d2a73bbcab64324abe88a69d157d6bd
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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