Sodium hydride → HCID 86674594, compound

HRID 2170706Notes

Reaction equation

HRID 2170706 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.Br[CH2:19][C:20]1[CH:21]=[C:22]([CH:30]=[CH:31][CH:32]=1)[O:23][C@@H:24]([CH3:29])[C:25]([O:27][CH3:28])=[O:26].[H-].[Na+]>CN(C=O)C>[CH3:28][O:27][C:25](=[O:26])[C@@H:24]([O:23][C:22]1[CH:21]=[C:20]([CH:32]=[CH:31][CH:30]=1)[CH2:19][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])[CH3:29]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27187797HCID 27187797, compoundHCID 86674593HCID 86674593, compound

Product 1

HCID 86674594HCID 86674594, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of allyl 2,3-dimethyl-1H-indole-5-carboxylate (1.0 g, 4.4 mmol, 1 equiv) and (S)-methyl 2-(3-(bromomethyl)phenoxy)propanoate (1.30 g, 4.84 mmol, 1.1 equiv) in anhydrous DMF (30 mL) under argon atmosphere was added sodium hydride (211 mg, 8.8 mmol, 2 equiv) in small portions. The mixture was stirred 2 h at room temperature. The reaction mixture was then quenched slowly with a solution of HCl 0.5 N. The residue was dissolved in AcOEt, washed with a saturated NaHCO3 solution and brine, dried over MgSO4. The crude was purified by flash chromatography (AcOEt/Hexane 0->60%) to afford the title compound.

Workup

  1. customThe reaction mixture was then quenched slowly with a solution of HCl 0.5 N
  2. dissolutionThe residue was dissolved in AcOEt
  3. washwashed with a saturated NaHCO3 solution and brine
  4. dry with materialdried over MgSO4
  5. customThe crude was purified by flash chromatography (AcOEt/Hexane 0->60%)

Sources & evidence

ORD record
ord-05f589fde4394f67a6539e527a6a8f5f
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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