N-bromobutanimide → 3-bromo-5-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 1926635Notes

Reaction equation

HRID 1926635 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[CH:15]=[CH:14][N:13]([S:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)(=[O:18])=[O:17])[C:10]3=[N:11][CH:12]=2)[CH:4]=[N:3]1.[Br:25]N1C(=O)CCC1=O>O1CCCC1>[Br:25][C:15]1[C:9]2[C:10](=[N:11][CH:12]=[C:7]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[CH:8]=2)[N:13]([S:16]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH:14]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 575024111H-Pyrrolo[2,3-b]pyridine, 5-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-

Product 1

HCID 575024123-bromo-5-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (0.832 g, 2.46 mmol) in tetrahydrofuran (12.3 ml) was added N-bromosuccinimide (0.875 g, 4.92 mmol). The reaction mixture was stirred at room temperature for 16 hours. The reaction was quenched with 10% aqueous sodium thiosulfate solution (50 mL), then extracted with EtOAc (2×50 mL). The combined organic layers were dried over magnesium sulfate, filtered and concentrated. The crude residue was adsorbed on to silica gel and purified by silica gel chromatography (EtOAc/Hexanes gradient) to afford 3-bromo-5-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine as a white solid. LRMS (ESI) calculated for C17H13BrN4O2S [M+H]+, 417.0; found 417.0.

Workup

  1. customThe reaction was quenched with 10% aqueous sodium thiosulfate solution (50 mL)
  2. extractionextracted with EtOAc (2×50 mL)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (EtOAc/Hexanes gradient)

Sources & evidence

ORD record
ord-fb0ab06a099b434b8ae297900f67e861
Source dataset
uspto-grants-2012_05
Patent number
US08183245B2

Reaction notes

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