Sodium hydride → HCID 86674586, compound

HRID 2170657Notes

Reaction equation

HRID 2170657 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH3:11])=[CH:8][C:7]([C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])=[CH:6][CH:5]=2.[H-].[Na+].Br[CH2:21][C:22]1[CH:23]=[C:24]([CH:32]=[CH:33][C:34]=1[Cl:35])[O:25][C@@H:26]([CH3:31])[C:27]([O:29][CH3:30])=[O:28]>CN(C=O)C.CCOC(C)=O>[Cl:35][C:34]1[CH:33]=[CH:32][C:24]([O:25][C@@H:26]([CH3:31])[C:27]([O:29][CH3:30])=[O:28])=[CH:23][C:22]=1[CH2:21][N:3]1[C:4]2[C:9](=[CH:8][C:7]([C:12]([O:14][CH2:15][CH:16]=[CH2:17])=[O:13])=[CH:6][CH:5]=2)[C:10]([CH3:11])=[C:2]1[CH3:1]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27187797HCID 27187797, compoundHCID 86674588HCID 86674588, compound

Product 1

HCID 86674586HCID 86674586, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the allyl 2,3-dimethyl-1H-indole-5-carboxylate (0.34 g, 1.483 mmol) in anhydrous DMF (3 mL) at 0° C. under argon protection was added NaH (0.08 g, 2.22 mmol). The mixture was stirred at rt for 30 min and re-cooled to 0° C., and then the (S)-methyl 2-(3-(bromomethyl)-4-chlorophenoxy)propanoate (0.55 g, 1.78 mmol) was added. The reaction was stirred at rt for another 1 h. The solvent was removed to obtain the crude, which was dissolved in EtOAc, then washed with water and brine and dried over Na2SO4. The solvent was removed to obtain the crude. The crude was purified by flash chromatography (AcOEt/Hexane 0-100%) to obtain the title compound. ESI-MS (m/z): 456 [M+1]+.

Workup

  1. temperaturere-cooled to 0° C.
  2. stirringThe reaction was stirred at rt for another 1 h
  3. customThe solvent was removed
  4. customto obtain the crude, which
  5. washwashed with water and brine
  6. dry with materialdried over Na2SO4
  7. customThe solvent was removed
  8. customto obtain the crude
  9. customThe crude was purified by flash chromatography (AcOEt/Hexane 0-100%)

Sources & evidence

ORD record
ord-523b7a85a4ed4bf6acbec41cb21c9a87
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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