Sodium Azide → HCID 71284622, compound

HRID 1481742Notes

Reaction equation

HRID 1481742 reaction equation
[CH3:1][O:2][C:3]1[CH:39]=[C:38]([O:40][CH3:41])[CH:37]=[CH:36][C:4]=1[CH2:5][N:6]1[C:11]([C:12]2[CH:13]=[C:14]3[C:18](=[CH:19][CH:20]=2)[N:17]([CH3:21])[C:16]([CH2:22][CH2:23]OS(C)(=O)=O)=[CH:15]3)=[C:10]([CH2:29][CH3:30])[CH:9]=[C:8]([C:31]([O:33][CH3:34])=[O:32])[C:7]1=[O:35].[N-:42]=[N+:43]=[N-:44].[Na+]>CS(C)=O.O>[N:42]([CH2:23][CH2:22][C:16]1[N:17]([CH3:21])[C:18]2[C:14]([CH:15]=1)=[CH:13][C:12]([C:11]1[N:6]([CH2:5][C:4]3[CH:36]=[CH:37][C:38]([O:40][CH3:41])=[CH:39][C:3]=3[O:2][CH3:1])[C:7](=[O:35])[C:8]([C:31]([O:33][CH3:34])=[O:32])=[CH:9][C:10]=1[CH2:29][CH3:30])=[CH:20][CH:19]=2)=[N+:43]=[N-:44]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 89422916HCID 89422916, compound

Product 1

HCID 71284622HCID 71284622, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To solution of methyl 1-(2,4-dimethoxybenzyl)-5-ethyl-6-(1-methyl-2-(2-(methylsulfonyloxy)ethyl)-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylate (309.6 mg, 0.53 mmol), prepared according to procedure described in Example 159 Step 10, in DMSO (2 mL) was added NaN3 (100 mg, 1.54 mmol). The reaction mixture was heated at 80° C. for 1.5 h until complete consumption of starting material was observed. The reaction mixture was then diluted with H2O and the product was extracted with DCM (3×10 mL). The combined organics were washed with NaCl (aqueous saturated, 5 mL) and dried over Na2SO4. Upon solvent removal, the residue was purified by column chromatography using EtOAc/hexanes (gradient 0-80%) to afford methyl 6-(2-(2-azidoethyl)-1-methyl-1H-indol-5-yl)-1-(2,4-dimethoxybenzyl)-5-ethyl-2-oxo-1,2-dihydropyridine-3-carboxylate (204.0 mg) in 73% yield. The product could not be completely separated from mesylate elimination by-product.

Workup

  1. extractionthe product was extracted with DCM (3×10 mL)
  2. washThe combined organics were washed with NaCl (aqueous saturated, 5 mL)
  3. dry with materialdried over Na2SO4
  4. customUpon solvent removal
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-89c57f4a438b4379a29c9832e1798c76
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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