Sodium hydride → HCID 67245854, compound

HRID 2425001Notes

Reaction equation

HRID 2425001 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][CH:9]=[C:8]2[CH3:14].[C:15]([NH:18][C:19]1[CH:20]=[C:21]([S:27](Cl)(=[O:29])=[O:28])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26])(=[O:17])[CH3:16]>O1CCCC1>[C:15]([NH:18][C:19]1[CH:20]=[C:21]([S:27]([N:10]2[C:11]3[C:7](=[CH:6][C:5]([O:4][CH3:3])=[CH:13][CH:12]=3)[C:8]([CH3:14])=[CH:9]2)(=[O:29])=[O:28])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26])(=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 77351Benzenesulfonyl chloride, 3-(acetylamino)-4-methoxy-HCID 111374445-methoxy-3-methyl-1H-indole

Product 1

HCID 67245854HCID 67245854, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Sodium hydride (2.15 grams, 49.3 mmol) was taken into a 250 mL three-necked round bottom flask containing tetrahydrofuran (50 mL) under nitrogen atmosphere. Added a solution of 5-methoxy-3-methyl indole solution (5.3 grams, 32.9 mmol) in tetrahydrofuran (25 mL) to the above mixture at 25° C., over a period of 15 minutes. The above reaction mass was stirred further for a period of 1 hour and mass was cooled to 0° C. and a solution of 3-acetamido-4-methoxy benzenesulfonyl chloride (13.01 grams, 49.3 mmol) in tetrahydrofuran (65 mL) was added through a dropping funnel over a period of 20 minutes. This mass was allowed to cool to room temperature and stirred over night (˜24 hours). The progress of the reaction was monitored by thin layer chromatography. After completion of the reaction it was quenched into ice water (100 mL) under stirring and extracted the product with ethylacetate (2×250 mL). Organic phase was washed with brine solution, dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain thick syrupy mass, which was used as such for the next step without purification.

Workup

  1. customThe above reaction mass
  2. temperatureto cool to room temperature
  3. stirringstirred over night (˜24 hours)
  4. customAfter completion of the reaction it
  5. customwas quenched into ice water (100 mL)
  6. stirringunder stirring
  7. extractionextracted the product with ethylacetate (2×250 mL)
  8. washOrganic phase was washed with brine solution
  9. dry with materialdried over anhydrous sodium sulphate
  10. concentrationconcentrated under reduced pressure
  11. customto obtain thick syrupy mass, which
  12. customwithout purification

Sources & evidence

ORD record
ord-f4ff7d9f64fd4e748f60f00434b9bd04
Source dataset
uspto-grants-2011_06
Patent number
US07964627B2

Reaction notes

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