Benzenesulfonyl chloride → 1-Benzenesulfonyl-5-(3-fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridine

HRID 493153Notes

Reaction equation

HRID 493153 reaction equation
CCCCCC.[F:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:15]=[C:16]3[CH:22]=[CH:21][NH:20][C:17]3=[N:18][CH:19]=2)[CH:11]=[CH:12][CH:13]=1.[C:23]1([S:29](Cl)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:23]1([S:29]([N:20]2[C:17]3=[N:18][CH:19]=[C:14]([C:10]4[CH:11]=[CH:12][CH:13]=[C:8]([F:7])[CH:9]=4)[CH:15]=[C:16]3[CH:22]=[CH:21]2)(=[O:31])=[O:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8058HexaneHCID 103079645-(3-Fluorophenyl)-1h-pyrrolo[2,3-b]pyridine

Product 1

HCID 578917421-Benzenesulfonyl-5-(3-fluoro-phenyl)-1H-pyrrolo[2,3-b]pyridineYield 92.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.5 M solution of n-Bui in hexane (2.47 mL, 6.18 mmol) was added dropwise to a stirred and cooled (−78° C.) solution of azaindole 7 (1.088 g, 5.13 mmol) in THF (5.5 mL). After the mixture was stirred for 20 min at −78° C., neat PhSO2Cl (0.785 mL, 6.2 mmol) was added dropwise. The mixture turned brown. Stirring at −78° C. was continued for 0.5 b. Cooling bath was removed, the mixture was stirred at r.t. overnight, and separated between AcOEt:saturated aqueous NaHCO3 solution. The aqueous layer was extracted with AcOEt (2×5 mL). Combined organic solutions were washed with brine, dried (MgSO4), concentrated, and separated by means of SGC with hexane:AcOEt as eluent in gradient to afford 12 (1.6705 g, 92%) as white solid. 1H NMR (400 MHz, CDCl3) δ 6.66 (d, J=4.0 Hz, 1H), 7.08 (dddd, J=8.4, 8.0, 2.5, 1.1 Hz, 1H), 7.25 (ddd, J=9.9, 2.5, 1.7 Hz, 1H), 7.33 (ddd, J=7.8, 1.7, 1.1 Hz, 1H), 7.43 (ddd, J=8.0, 7.8, 6.0 Hz, 1H), 7.47-7.53 (m, 2H), 7.57-7.62 (m, 1H), 7.78 (d, J=4.0 Hz, 1H), 7.99 (d, J=2.2 Hz, 1H), 8.21-8.26 (m, 2H), 8.63 (d, J=2.2 Hz, 1H).

Workup

  1. stirringAfter the mixture was stirred for 20 min at −78° C.
  2. stirringStirring at −78° C.
  3. temperatureCooling bath
  4. customwas removed
  5. stirringthe mixture was stirred at r.t. overnight
  6. customseparated between AcOEt
  7. extractionThe aqueous layer was extracted with AcOEt (2×5 mL)
  8. washCombined organic solutions were washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customseparated by means of SGC with hexane

Sources & evidence

ORD record
ord-0d72aea1150c42d3b6cd15d4052fd547
Source dataset
uspto-grants-2009_05
Patent number
US07534800B2

Reaction notes

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