Sodium Sulfate → HCID 53258906, compound

HRID 1474425Notes

Reaction equation

HRID 1474425 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([S:11]([C:14]3[CH:15]=[CH:16][C:17]([CH3:21])=[C:18]([NH2:20])[CH:19]=3)(=[O:13])=[O:12])=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:22][N:23]1[CH2:28][CH2:27][C:26](=O)[CH2:25][CH2:24]1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(O)(=O)C>[CH3:21][C:17]1[CH:16]=[CH:15][C:14]([S:11]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=3)[NH:8][CH:7]=2)(=[O:13])=[O:12])=[CH:19][C:18]=1[NH:20][CH:26]1[CH2:27][CH2:28][N:23]([CH3:22])[CH2:24][CH2:25]1

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 740491-Methyl-4-piperidoneHCID 5049666Sodium triacetoxyborohydrideHCID 67343742HCID 67343742, compound

Product 1

HCID 53258906HCID 53258906, compoundYield 39.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
30 °C

Procedure

5-(6-Chloro-1H-indole-3-yl sulfonyl)-2-methyl phenyl amine [obtained from preparation 1, Step (v)](600 mg, 1.87 mmol) was added to a 100 mL three necked round bottomed flask, followed by the addition of 1-methyl-4-piperidone (423 mg, 3.74 mmol), sodium sulfate (2.6 grams, 18.7 mmol) and acetic acid (12 mL). The reaction mass was stirred for 4 hours at room temperature (30° C.). Then sodium tri acetoxy borohydride (1.18 grams, 5.61 mmol) was added to the reaction mass at 20-25° C. in 5 minutes. This reaction mixture was further stirred over night at room temperature. The reaction mixture was then quenched into 100 mL water, basified to pH 9 with 50% aqueous sodium hydroxide solution under cooling (10° C.) and extracted the product with ethylacetate (4×50 mL). The combined organic layer was washed with saturated brine solution (2×50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to obtain oily mass. The technical product was further purified by column chromatography using ethylacetate and methanol as an eluents to obtain 0.31 grams of the title product.

Workup

  1. stirringThis reaction mixture was further stirred over night at room temperature
  2. customThe reaction mixture was then quenched into 100 mL water
  3. temperatureunder cooling (10° C.)
  4. extractionextracted the product with ethylacetate (4×50 mL)
  5. washThe combined organic layer was washed with saturated brine solution (2×50 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under vacuum
  9. customto obtain oily mass
  10. customThe technical product was further purified by column chromatography

Sources & evidence

ORD record
ord-66dfd3b7270d40589aa6ebe0ee9ce8af
Source dataset
uspto-grants-2015_04
Patent number
US09018231B2

Reaction notes

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