Sodium borohydride → HCID 10090317, compound

HRID 1293472Notes

Reaction equation

HRID 1293472 reaction equation
C([N:3]1[C:15]2[C:14]([O:16][CH3:17])=[CH:13][CH:12]=[C:11]([S:18]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)(=[O:20])=[O:19])[C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)=O.[BH4-].[Na+]>C1COCC1>[CH3:17][O:16][C:14]1[C:15]2[NH:3][C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:10]=2[C:11]([S:18]([NH:21][C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)(=[O:19])=[O:20])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10046153HCID 10046153, compound

Product 1

HCID 10090317HCID 10090317, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-Formyl-1-methoxy-4-[4-methylphenylaminosulphonyl]-9H-carbazole (example 72) (0.14 g, 0.35 mM) was dissolved in 15 mL of 20% aqueous THF solution. The reaction mixture was cooled to 0° C. in an ice bath. To it was added NaBH4 (0.08 g, 2.1 mM) portion wise. The reaction mixture was stirred for 4-5 hrs. Solvent was evaporated and the aqueous layer was extracted with EtOAc. The organic layer was washed with brine and dried over anh. Na2SO4. It was filtered and concentrated to yield the desired compound as a white solid with a yield of 99% (0.13 g). mp 199-203° C.

Workup

  1. customSolvent was evaporated
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anh. Na2SO4
  5. filtrationIt was filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-57f2b7411a1640808c61bff913a736b0
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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