Iodine → 6-methyl-3-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-ylsulfanyl]-[1,2,4]triazolo[4,3-b]pyridazine

HRID 1890964Notes

Reaction equation

HRID 1890964 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[CH:15]=[CH:14][NH:13][C:10]3=[N:11][CH:12]=2)[CH:4]=[N:3]1.[CH3:16][C:17]1[CH:18]=[CH:19][C:20]2[N:21]([C:23]([SH:26])=[N:24][N:25]=2)[N:22]=1.II>CN(C=O)C>[CH3:16][C:17]1[CH:18]=[CH:19][C:20]2[N:21]([C:23]([S:26][C:15]3[C:9]4[C:10](=[N:11][CH:12]=[C:7]([C:5]5[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=5)[CH:8]=4)[NH:13][CH:14]=3)=[N:24][N:25]=2)[N:22]=1

Participants

5

Reactant 3

HCID 807IodineHCID 580861115-(1-Methyl-1H-pyrazol-4-YL)-1H-pyrrolo[2,3-B]pyridineHCID 178423528HCID 178423528, compound

Product 1

HCID 249011166-methyl-3-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-ylsulfanyl]-[1,2,4]triazolo[4,3-b]pyridazineYield 11.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine (28 mg, 0.141 mmol) and 6-methyl-[1,2,4]triazolo[4,3-b]pyridazine-3-thiol (35.3 mg, 0.212 mmol) in DMF (700 μL) was added iodine (72 μL, 0.283 mmol). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was then filtered and purified by mass-triggered HPLC (5-95% CH3CN/H2O, 0.1% HCOOH modifier) to provide 5.7 mg of 6-methyl-3-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-ylsulfanyl]-[1,2,4]triazolo[4,3-b]pyridazine (11% yield).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. custompurified by mass-triggered HPLC (5-95% CH3CN/H2O, 0.1% HCOOH modifier)

Sources & evidence

ORD record
ord-5eca4736c8a24ff09ddb7684d06b0541
Source dataset
uspto-grants-2013_08
Patent number
US08507489B2

Reaction notes

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