Benzenesulfonyl chloride → HCID 58266575, compound

HRID 1505850Notes

Reaction equation

HRID 1505850 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([Br:14])[CH:12]=2)[NH:7][CH:6]=1)=[O:4].[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>C1COCC1.C(=O)([O-])[O-].[Na+].[Na+]>[CH3:1][O:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([Br:14])[CH:12]=2)[N:7]([S:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:23])=[O:22])[CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 16202927Methyl 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylate

Product 1

HCID 58266575HCID 58266575, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Procedure

A mixture of 5-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxylic acid methyl ester (15.0 mmol), benzenesulfonyl chloride (11.9 g, 8.61 mL, 67.5 mmol) and triethylamine (9.61 g, 13.2 mmol) in dry THF (100 mL) was heated under reflux for 19 h. The resultant suspension was allowed to cool to ambient temperature and diluted with saturated aqueous sodium carbonate solution (50 mL) and extracted with DCM (2×50 mL) and THF (1×50 mL). The combined organic phase was dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash chromatography (silica, 50 g cartridge, Si-SPE, 0-100% DCM in pentane). The relevant fractions were concentrated in vacuo and the residue was triturated with pentane (10 mL) to afford the title compound as a white solid (5.25 g, 88%). LCMS (Method B): RT=4.11 min, M+H+=395/397.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 19 h
  3. extractionextracted with DCM (2×50 mL) and THF (1×50 mL)
  4. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe resultant residue was purified by flash chromatography (silica, 50 g cartridge, Si-SPE, 0-100% DCM in pentane)
  7. concentrationThe relevant fractions were concentrated in vacuo
  8. customthe residue was triturated with pentane (10 mL)

Sources & evidence

ORD record
ord-ab251a354344403ba05098d18aef4c35
Source dataset
uspto-grants-2015_12
Patent number
US09216980B2

Reaction notes

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