Sodium cyanoborohydride → HCID 87604005, compound

HRID 2102694Notes

Reaction equation

HRID 2102694 reaction equation
C([BH3-])#N.[Na+].[C:5]([O:9][C:10]([N:12]1[CH:17]=[C:16]([C:18]2([CH2:29][C:30]3[CH:35]=[C:34]([Cl:36])[N:33]=[C:32]([Cl:37])[CH:31]=3)[C:26]3[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=3)[NH:20][C:19]2=[O:28])[CH2:15][CH2:14][CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6]>C(O)(=O)C>[C:5]([O:9][C:10]([N:12]1[CH:17]=[C:16]([C:18]2([CH2:29][C:30]3[CH:35]=[C:34]([Cl:36])[N:33]=[C:32]([Cl:37])[CH:31]=3)[C:26]3[C:21](=[CH:22][C:23]([Cl:27])=[CH:24][CH:25]=3)[NH:20][C:19]2=[O:28])[CH:15]=[CH:14][CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 11998147HCID 11998147, compound

Product 1

HCID 87604005HCID 87604005, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

Sodium cyanoborohydride (0.37 g, 5.89 mmol) was added to a solution of rac-5-[6-chloro-3-(2,6-dichloro-pyridin-4-ylmethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (0.3 g, 0.589 mmol) (from Example 23 supra) in acetic acid (6 mL). The mixture was heated at 60° C. for 16 hours. After cooling, the solvent was evaporated in vacuo. To the residue was added saturated aqueous sodium bicarbonate solution, and extracted three times with ethyl acetate. The organic layers were separated, combined, dried over Na2SO4 and concentrated. The residue was purified by chromatography (ethyl acetate-dichloromethane, 1:9, V/V) to give rac-5-[6-chloro-3-(2,6-dichloro-pyridin-4-ylmethyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-pyridine-1-carboxylic acid tert-butyl ester as a white solid. (Yield 0.2 g, 67%). Further purification by recrystallization from dichloromethane-hexanes gave the product as a white solid. (Yield 0.075 g).

Workup

  1. temperatureAfter cooling
  2. customthe solvent was evaporated in vacuo
  3. additionTo the residue was added saturated aqueous sodium bicarbonate solution
  4. extractionextracted three times with ethyl acetate
  5. customThe organic layers were separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (ethyl acetate-dichloromethane, 1:9, V/V)

Sources & evidence

ORD record
ord-371512ea552f4573ab9562adb61873c2
Source dataset
uspto-grants-2009_08
Patent number
US07576082B2

Reaction notes

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