Sodium Hydroxide → HCID 11590985, compound

HRID 1677833Notes

Reaction equation

HRID 1677833 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[CH:18]([NH2:22])[CH:19]([CH3:21])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[BH-](O[C:33](=[O:35])[CH3:34])OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl>[NH2:8][CH2:1][CH2:2][CH2:3][N:22]([CH:18]([C:9]1[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:16]2[C:11]([CH:10]=1)=[CH:12][C:13]([Cl:17])=[CH:14][CH:15]=2)[CH:19]([CH3:20])[CH3:21])[C:33](=[O:35])[C:34]1[CH:19]=[CH:18][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 57894430HCID 57894430, compound

Product 1

HCID 11590985HCID 11590985, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(1-benzyl-5-chloro-1H-indole-2-yl)-2-methylpropan-1-amine (0.44 mmol) in 10 mL of anhydrous DCM, was added aldehyde (0.44 mmol) and sodium triacetoxyborohydride (0.44 mmol) at 0° C. The mixture was stirred at room temperature overnight. The solution was poured into 10% aq. NaOH, and extracted with EtOAc (×3). The organic layers were combined, washed with H2O (×3), brine (×3), dried (Na2SO4), filtered, and the filtrate was concentrated. The material was purified by flash chromatography (20% EtOAc:hexane) to yield 40 mg of title compound.

Workup

  1. extractionextracted with EtOAc (×3)
  2. washwashed with H2O (×3), brine (×3)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe material was purified by flash chromatography (20% EtOAc:hexane)

Sources & evidence

ORD record
ord-595b73d026634dc7abc67b22dfe3fbe5
Source dataset
uspto-grants-2011_08
Patent number
US08008335B2

Reaction notes

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