o-Toluenesulfonyl chloride → HCID 57537464, compound

HRID 1693705Notes

Reaction equation

HRID 1693705 reaction equation
[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:6][N:5]=[C:4]2[NH:19][CH:20]=[CH:21][C:3]=12.[I:22]N1C(=O)CCC1=O.[H-].[Na+].[C:32]1([CH3:42])[C:33](S(Cl)(=O)=O)=[CH:34][CH:35]=[CH:36][CH:37]=1.[S:43]([O-:47])([O-])(=[O:45])=S.[Na+].[Na+]>CC(C)=O.O>[Cl:1][C:2]1[C:7]([C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([N:13]([CH3:15])[CH3:14])=[O:12])=[CH:6][N:5]=[C:4]2[N:19]([S:43]([C:35]3[CH:34]=[CH:33][C:32]([CH3:42])=[CH:37][CH:36]=3)(=[O:47])=[O:45])[CH:20]=[C:21]([I:22])[C:3]=12

Participants

8

Reactant 5

HCID 8623o-Toluenesulfonyl chlorideHCID 24477Sodium ThiosulfateHCID 24758Sodium hydrideHCID 120273N-IodosuccinimideHCID 57537575HCID 57537575, compound

Product 1

HCID 57537464HCID 57537464, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

3-(4-Chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)-N,N-dimethyl-benzamide (148 mg, 0.5 mmol) was dissolved in 3.5 mL acetone, and N-iodosuccinimide (133 mg, 0.6 mmol) was added. The suspension was stirred for 1 h at 23° C., diluted with water and sodium thiosulfate solution, filtered, and washed with water. The yellow powder was dissolved in 5 mL dry DMF and sodium hydride (30 mg, 0.75 mmol) was added. After the gas evolution subsided (10 min), toluenesulfonyl chloride (141 mg, 0.75 mmol) was added. The mixture was stirred at 60° C. for 12 h and quenched with saturated ammonium chloride solution. The suspension was filtered and washed with water to afford 3-[4-Chloro-3-iodo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide as a light brown solid (310 mg, 0.49 mmol, quantitative). 1H NMR (500 MHz, DMSO-d6) δ 8.38 (s, 1H), 8.28 (s, 1H), 8.05 (m, 2H), 7.44-7.56 (m, 6H), 2.97 (bs, 3H), 2.93 (bs, 3H), 2.36 (s, 3H). MS: m/z 580.2 (M+H).

Workup

  1. filtrationfiltered
  2. washwashed with water
  3. dissolutionThe yellow powder was dissolved in 5 mL dry DMF
  4. additionwas added
  5. stirringThe mixture was stirred at 60° C. for 12 h
  6. customquenched with saturated ammonium chloride solution
  7. filtrationThe suspension was filtered
  8. washwashed with water

Sources & evidence

ORD record
ord-af12fa1cca1f470a9bd48f912fa172dd
Source dataset
uspto-grants-2012_04
Patent number
US08158647B2

Reaction notes

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