Sodium Bicarbonate → 4-(3-Cyano-5-hydroxymethylindol-1-yl)benzoic acid ethyl ester

HRID 73369Notes

Reaction equation

HRID 73369 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20](O)=[O:21])=[CH:17][CH:18]=3)[C:13]([C:23]#[N:24])=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2].B.O1CCCC1.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH2:1]([O:3][C:4](=[O:25])[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:19]3[C:14](=[CH:15][C:16]([CH2:20][OH:21])=[CH:17][CH:18]=3)[C:13]([C:23]#[N:24])=[CH:12]2)=[CH:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2723981Borane;tetrahydrofuranHCID 58437256HCID 58437256, compound

Product 1

HCID 584373394-(3-Cyano-5-hydroxymethylindol-1-yl)benzoic acid ethyl esterYield 58.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(5-carboxy-3-cyanoindol-1-yl)benzoic acid ethyl ester (0.057 g) in tetrahydrofuran (2 mL) was added borane-tetrahydrofuran complex (1.2 mol/L tetrahydrofuran solution 0.2 mL) at 0° C. and this mixture was stirred at room temperature for 2 hours. To this reaction mixture was added a saturated aqueous sodium bicarbonate solution, this mixture was extracted with diethyl ether. This organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/1) to give the title compound (0.032 g).

Workup

  1. extractionthis mixture was extracted with diethyl ether
  2. washThis organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/n-hexane=1/1)

Sources & evidence

ORD record
ord-76572caf4aee43809fed7f10dff5308d
Source dataset
uspto-grants-2014_09
Patent number
US08829040B2

Reaction notes

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