Benzenesulfonyl chloride → 1-(Phenylsulfonyl)-1H-pyrrolo[3,2-c]pyridine

HRID 1922728Notes

Reaction equation

HRID 1922728 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][N:6]=[CH:5][C:4]=2[CH:3]=[CH:2]1.C1COCC1.[C:15]1([S:21](Cl)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[C:15]1([S:21]([N:1]2[C:9]3[CH:8]=[CH:7][N:6]=[CH:5][C:4]=3[CH:3]=[CH:2]2)(=[O:23])=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 92205-Azaindole

Product 1

HCID 110106571-(Phenylsulfonyl)-1H-pyrrolo[3,2-c]pyridineYield 59.5%

Procedure

A 100 mL round-bottomed flask was charged with a solution of 1H-pyrrolo[3,2-c]pyridine (1.0 g, 8.4 mmol) in anhydrous THF (50 mL) NaH (60% in mineral oil, 0.41 g, 10.2 mmol) was added and the reaction mixture was stirred for 5 min at room temperature. To this solution was added dropwise, at 0° C., benzenesulfonyl chloride (1.35 mL, 10.2 mmol) and the resulting mixture was stirred at room temperature for 2 h. The reaction mixture was quenched with water (30 mL) and extracted with EtOAc (3×100 mL) The organic layers were combined, dried (Na2SO4) and concentrated in vacuo to give the title compound as a white solid (1.29 g, 55%). 1H NMR (DMSO, 300 MHz): δ 8.95 (s, 1 H); 8.49 (d, J=5.8 Hz, 1 H); 8.13-8.05 (m, 2 H); 8.02-7.94 (m, 2 H); 7.79-7.71 (m, 1 H); 7.69-7.59 (m, 2 H); 7.01 (dd, J=3.7, 0.9 Hz, 1 H).

Workup

  1. additionwas added
  2. additionTo this solution was added dropwise, at 0° C.
  3. customThe reaction mixture was quenched with water (30 mL)
  4. extractionextracted with EtOAc (3×100 mL) The organic layers
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-31c48da6e8574413bcb03b730b849ae0
Source dataset
uspto-grants-2012_05
Patent number
US08173650B2

Reaction notes

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