Sodium borohydride → HCID 22660576, compound

HRID 392756Notes

Reaction equation

HRID 392756 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]([C:10]2[NH:11][C:12]3[C:17]([C:18]=2[CH:19]=[O:20])=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[CH2:4][CH2:3]1.[BH4-].[Na+]>C(OCC)(=O)C>[OH:20][CH2:19][C:18]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][C:10]=1[C:8]([N:5]1[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]1)=[O:9]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22660605HCID 22660605, compound

Product 1

HCID 22660576HCID 22660576, compoundYield 44.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-(4-Methyl-piperazine-1-carbonyl)-1H-indole-3-carbaldehyde (Example 51, 0.094 g) in ethyl acetate (1.5 mL) was treated with sodium borohydride (0.024 g) and stirred at ambient temperature for 3 h. The solvent was removed under reduced pressure, and the residue treated with saturated sodium hydrogencarbonate solution and extracted with dichloromethane. The organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified via silica gel chromatography, eluting with 1-8% methanol/dichloromethane, to afford the title compound (0.042 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue treated with saturated sodium hydrogencarbonate solution
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via silica gel chromatography
  8. washeluting with 1-8% methanol/dichloromethane

Sources & evidence

ORD record
ord-bcd556e08bdb480a99b1eef201868638
Source dataset
uspto-grants-2004_10
Patent number
US06803362B2

Reaction notes

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