Sodium Carbonate → HCID 57502422, compound

HRID 1926642Notes

Reaction equation

HRID 1926642 reaction equation
C(OC([N:8]1[CH:12]=[C:11](B2OC(C)(C)C(C)(C)O2)[CH:10]=[N:9]1)=O)(C)(C)C.Br[C:23]1[CH:24]=[C:25]2[CH:31]=[CH:30][N:29]([S:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C:26]2=[N:27][CH:28]=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>[C:35]1([S:32]([N:29]2[C:26]3=[N:27][CH:28]=[C:23]([C:11]4[CH:12]=[N:8][NH:9][CH:10]=4)[CH:24]=[C:25]3[CH:31]=[CH:30]2)(=[O:34])=[O:33])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 16217654tert-butyl 4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylateHCID 242292461-(Benzenesulfonyl)-5-bromo-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 57502422HCID 57502422, compound

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 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2yl)-pyrazole-1-carboxylic acid tert-butyl ester (1.31 g, 4.45 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 1 hour. The reaction mixture was cooled to room temperature and partitioned between EtOAc (50 mL) and saturated aqueous ammonium chloride (50 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 1-(phenylsulfonyl)-5-(1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine as a yellow solid. LRMS (ESI) calculated for C16H12N4O2S [M+H]+, 325.1; found 325.0.

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 (50 mL) and saturated aqueous ammonium chloride (50 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-6d301fe2b57c4b549e21918f47d98ecc
Source dataset
uspto-grants-2012_05
Patent number
US08183245B2

Reaction notes

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