Sodium borohydride → HCID 10045440, compound

HRID 1293470Notes

Reaction equation

HRID 1293470 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]([O:28][CH3:29])=[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]([O:28][CH3:29])=[CH:26][CH:27]=2)(=[O:19])=[O:20])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10476669HCID 10476669, compound

Product 1

HCID 10045440HCID 10045440, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-Formyl-1-methoxy-4-[4-methoxyphenylaminosulphonyl]-9H-carbazole (example 70) (0.1 g, 0.24 mM) was dissolved in 18 mL of 20% aqueous THF solution. The reaction mixture was cooled to 0° C. in an ice bath. To it was added NaBH4 (0.055 g, 1.45 mM) portion wise. The reaction mixture was stirred overnight 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 crude product. The crude product was purified over a silica gel column using EtOAc- hexane as a solvent system to yield the desired compound as a white semi-solid with a yield of 66% (0.062 g).

Workup

  1. customwas 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
  7. customto yield the crude product
  8. customThe crude product was purified over a silica gel column

Sources & evidence

ORD record
ord-43b1038c26ff45feabd295d0be3f33b1
Source dataset
uspto-grants-2007_07
Patent number
US07238725B2

Reaction notes

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