Aluminium lithium hydride → HCID 67002857, compound

HRID 1879668Notes

Reaction equation

HRID 1879668 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Br:7][C:8]1[CH:16]=[CH:15][C:14]([S:17]([N:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21]2)(=[O:19])=[O:18])=[CH:13][C:9]=1[C:10](O)=[O:11]>O1CCCC1.O>[Br:7][C:8]1[CH:16]=[CH:15][C:14]([S:17]([N:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21]2)(=[O:18])=[O:19])=[CH:13][C:9]=1[CH2:10][OH:11]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67002833HCID 67002833, compound

Product 1

HCID 67002857HCID 67002857, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a suspension of Lithium aluminium hydride (2.3 grams, 60.5 mmol) in tetrahydrofuran (20 mL) was added a solution of 2-bromo-5-(indole-1-sulfonyl) benzoic acid (17.64 grams, 46.42 mmol) (obtained from preparation 1) in tetrahydrofuran (30 mL) maintaining mass temperature at 0-5° C. The reaction mass was stirred at 0-5° C. for 4 hours. The progress of the reaction was followed by TLC. After completion of the reaction, the reaction mass was cooled to −10° C. Water (20 mL) was added water slowly under nitrogen atmosphere. The reaction mass was diluted further with water (300 mL) and filtered through hyflow bed. The clear filtrate was extracted with ethyl acetate (4×100 mL). The combined organic layer was washed with brine solution (2×50 mL), water (2×50 mL) and dried over anhydrous sodium sulphate and was concentrated under reduced pressure. The residual mass was purified by column chromatography, the eluent system being ethyl acetate and hexane (2:8) to obtain 6.025 gram the title product.

Workup

  1. customAfter completion of the reaction
  2. temperaturethe reaction mass was cooled to −10° C
  3. filtrationfiltered through hyflow bed
  4. extractionThe clear filtrate was extracted with ethyl acetate (4×100 mL)
  5. washThe combined organic layer was washed with brine solution (2×50 mL), water (2×50 mL)
  6. dry with materialdried over anhydrous sodium sulphate
  7. concentrationwas concentrated under reduced pressure
  8. customThe residual mass was purified by column chromatography

Sources & evidence

ORD record
ord-f58eadd4d44b41a0aa27d1e6259c67cb
Source dataset
uspto-grants-2012_11
Patent number
US08318725B2

Reaction notes

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