Phenylboronic Acid → 5-phenyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 549076Notes

Reaction equation

HRID 549076 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:11]1[CH:12]=[C:13]2[CH:19]=[CH:18][N:17]([S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[C:14]2=[N:15][CH:16]=1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:1]1([C:11]2[CH:12]=[C:13]3[CH:19]=[CH:18][N:17]([S:20]([C:23]4[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=4)(=[O:21])=[O:22])[C:14]3=[N:15][CH:16]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 224773531H-Pyrrolo[2,3-B]pyridine, 5-bromo-1-[(4-methylphenyl)sulfonyl]-

Product 1

HCID 224773445-phenyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of phenyl boronic acid (1.74 g), 5-bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine [5 g, Reference Example 9(d)], (tetrakis)triphenylphosphine palladium[0] (0.49 g) and saturated aqueous sodium bicarbonate solution (133 mL) and dimethylformamide (266 mL), under nitrogen, was heated at reflux temperature overnight. The reaction mixture was filtered through Hyflo and then evaporated. The residue was partitioned between ethyl acetate (50 mL) and water (25 mL) and the aqueous layer was extracted with ethyl acetate (25 mL). The combined organic phases were washed with water (25 mL), then with brine (20 mL), then dried over magnesium sulfate and then evaporated. The residue subjected to chromatography on silica eluting with a mixture of pentane and ether (1:1, v/v) to give the title compound as a white solid, mp. 151-152° C. MS: 335 (MH+).

Workup

  1. temperatureunder nitrogen, was heated
  2. temperatureat reflux temperature overnight
  3. filtrationThe reaction mixture was filtered through Hyflo
  4. customevaporated
  5. customThe residue was partitioned between ethyl acetate (50 mL) and water (25 mL)
  6. extractionthe aqueous layer was extracted with ethyl acetate (25 mL)
  7. washThe combined organic phases were washed with water (25 mL)
  8. dry with materialwith brine (20 mL), then dried over magnesium sulfate
  9. customevaporated
  10. additionThe residue subjected to chromatography on silica eluting with a mixture of pentane and ether (1:1

Sources & evidence

ORD record
ord-03ba36ee71e94c93ad6bd4b27c1c3ee0
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

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