4-Toluenesulfonyl chloride → N-(3-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide

HRID 531436Notes

Reaction equation

HRID 531436 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([I:11])=[CH:9][N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.IC1C2C(=NC=C([C:32]3[CH:33]=[C:34]([NH:38][S:39]([CH3:42])(=[O:41])=[O:40])[CH:35]=[CH:36][CH:37]=3)C=2)NC=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[H-].[Na+]>CN(C=O)C>[I:11][C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:32]3[CH:33]=[C:34]([NH:38][S:39]([CH3:42])(=[O:40])=[O:41])[CH:35]=[CH:36][CH:37]=3)[CH:3]=2)[N:8]([S:12]([C:15]2[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:9]=1

Participants

6

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 497590665-bromo-3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 90031153N-(3-(3-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide

Product 1

HCID 90030209N-(3-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using similar reaction conditions as described in, step ii of Intermediate 1, N-(3-(3-iodo-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)methanesulfonamide (800 mg, 1.93 mmol) was tosylated with p-toluene sulfonylchloride (100 mg, 2.09 mmol) and 60% suspension of sodium hydride in paraffin (193 mg, 4.82 mmol) in DMF (10 mL) to afford 800 mg of the titled compound.

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-c9b2e503d9ec4bbc8435a2b1e00e9103
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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