Benzenesulfonyl chloride → HCID 90413564, compound

HRID 1522000Notes

Reaction equation

HRID 1522000 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12.C(N(CC)CC)C.[C:20]1([S:26](Cl)(=[O:28])=[O:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[N:10]([S:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)(=[O:28])=[O:27])[CH:11]=[CH:12][C:3]=12

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 242292484-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile

Product 1

HCID 90413564HCID 90413564, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbonitrile (2.6 g, 14.64 mmol) and triethylamine (3.06 mL, 21.96 mmol) in tetrahydrofuran (100 mL) was cooled to 0° C. and benzenesulfonyl chloride (2.253 mL, 17.57 mmol) was added dropwise. The mixture was stirred at 0° C. for 1 hour and at room temperature for 10 hours and the mixture was concentrated. Water was added and the mixture was extracted with dichloromethane (three times). The organic phase was washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was triturated with diethyl ether to afford the title compound. MS (ESI(+)) m/e 318 (M+H)+.

Workup

  1. concentrationthe mixture was concentrated
  2. additionWater was added
  3. extractionthe mixture was extracted with dichloromethane (three times)
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-92e9244ada4949efac3899f9d8da2fe6
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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