Benzaldehyde → HCID 59625807, compound

HRID 401696Notes

Reaction equation

HRID 401696 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1.[CH:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl.O>[CH2:15]([N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 534083041H-Indole-5-carboxylic acid, 2,3-dihydro-, methyl ester, hydrochloride (1:1)

Product 1

HCID 59625807HCID 59625807, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of methyl 2,3-dihydro-1H-indole-5-carboxylate HCl salt 55a (88.6 mg, 0.42 mmol), and benzaldehyde 23a (0.060 mL, 0.55 mmol) in CH2Cl2 (4 mL) was stirred at room temperature for 30 min. Sodium triacetoxyborohydride (159 mg, 0.75 mmol) was added to the mixture and stirring was continued for 2 h. Water was added to the resulting mixture at 0° C., and pH of the solution was adjusted to ˜8 with 1N aqueous NaOH. The mixture was extracted with CH2Cl2 and the organic layer was washed with brine and dried over Na2SO4. The solution was concentrated and purified by flash column chromatography (silica gel, 10-25% EtOAc/Heptanes) to give 55e (81.3 mg). MS m/z (M+H+) 268.0.

Workup

  1. extractionThe mixture was extracted with CH2Cl2
  2. washthe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe solution was concentrated
  5. custompurified by flash column chromatography (silica gel, 10-25% EtOAc/Heptanes)

Sources & evidence

ORD record
ord-2169a3d990bc4fe6875419cbc9f46be5
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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