Potassium tert-butoxide → N-(4-Fluoro-benzyl)-4-(3-phenyl-pyrrolo[2,3-b]pyridine-1-sulfonyl)-benzamide

HRID 737050Notes

Reaction equation

HRID 737050 reaction equation
[C:1]1([C:7]2[C:15]3[C:10](=[N:11][CH:12]=[CH:13][CH:14]=3)[NH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[F:22][C:23]1[CH:42]=[CH:41][C:26]([CH2:27][NH:28][C:29]([C:31]2[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=2)=[O:30])=[CH:25][CH:24]=1>CN(C=O)C>[F:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:27][NH:28][C:29](=[O:30])[C:31]2[CH:36]=[CH:35][C:34]([S:37]([N:9]3[C:10]4=[N:11][CH:12]=[CH:13][CH:14]=[C:15]4[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:8]3)(=[O:38])=[O:39])=[CH:33][CH:32]=2)=[CH:41][CH:42]=1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 522706843-phenyl-1H-pyrrolo[2,3-b]pyridineHCID 589751254-(4-Fluoro-benzylcarbamoyl)-benzenesulfonyl chloride

Product 1

HCID 57849045N-(4-Fluoro-benzyl)-4-(3-phenyl-pyrrolo[2,3-b]pyridine-1-sulfonyl)-benzamideYield 18.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Slowly add 3-phenyl-1H-pyrrolo[2,3-b]pyridine (178 mg, 0.915 mmol, 1.0 eq) as a 2 ml DMF solution to a flask under N2 containing potassium tertbutoxide (108 mg, 0.961 mmol, 1.05 eq) in 1 ml DMF solution. Stir solution for 5 minutes. Slowly add 4-(4-Fluoro-benzylcarbamoyl)-benzenesulfonyl chloride (300 mg, 0.915 mmol, 1.0 eq) as a 3 ml DMF solution. Stir reaction for 18 hours at room temperature. Strip reaction of solvent and purify on silica gel chromatography to give N-(4-Fluoro-benzyl)-4-(3-phenyl-pyrrolo[2,3-b]pyridine-1-sulfonyl)-benzamide (82 mg, 18% yield). Mass Spectrum (m/e): 485.94 (MH+).

Workup

  1. customreaction for 18 hours at room temperature
  2. customStrip reaction of solvent
  3. custompurify on silica gel chromatography

Sources & evidence

ORD record
ord-68ba05dfeb7749cb8a7af22a0d2ae677
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

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