Sodium Carbonate → 1H-Pyrrolo[2,3-b]pyridine, 5-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-

HRID 1926634Notes

Reaction equation

HRID 1926634 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:4]=[N:3]1.Br[C:17]1[CH:18]=[C:19]2[CH:25]=[CH:24][N:23]([S:26]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)(=[O:28])=[O:27])[C:20]2=[N:21][CH:22]=1.C(=O)([O-])[O-].[Na+].[Na+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][N:2]1[CH:6]=[C:5]([C:17]2[CH:18]=[C:19]3[CH:25]=[CH:24][N:23]([S:26]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)(=[O:27])=[O:28])[C:20]3=[N:21][CH:22]=2)[CH:4]=[N:3]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 242292461-(Benzenesulfonyl)-5-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

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

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a degassed (sparging with argon for 5 minutes), stirred solution of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.617 g, 2.97 mmol) and 5-bromo-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1.00 g, 2.97 mmol) in dioxane (12.0 ml) was added Pd(Ph3P)4 (0.171 g, 0.148 mmol), followed by a degassed aqueous solution of sodium carbonate (4.45 ml, 8.90 mmol). The reaction mixture was stirred under nitrogen at 100° C. for 2 h. The reaction mixture was cooled to room temperature and partitioned between EtOAc (25 mL) and saturated aqueous ammonium chloride (25 mL). The organic layer was dried over magnesium sulfate, filtered and concentrated to a crude residue. The residue was purified by silica gel chromatography (EtOAc/Hexanes gradient) to afford 5-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine as a white solid. LRMS (ESI) calculated for C17H14N4O2S [M+H]+, 339.1; found 339.1.

Workup

  1. customTo a degassed
  2. custom(sparging with argon for 5 minutes)
  3. temperatureThe reaction mixture was cooled to room temperature
  4. custompartitioned between EtOAc (25 mL) and saturated aqueous ammonium chloride (25 mL)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to a crude residue
  8. customThe residue was purified by silica gel chromatography (EtOAc/Hexanes gradient)

Sources & evidence

ORD record
ord-4b9205c5847b4a28a7fc4dc399c4d1be
Source dataset
uspto-grants-2012_05
Patent number
US08183245B2

Reaction notes

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