Sodium → HCID 58019861, compound

HRID 2200074Notes

Reaction equation

HRID 2200074 reaction equation
[CH3:1][O-:2].[Na+].[Na].[NH2:5][C:6]1[N:14]=[C:13]([O:15][CH2:16][CH2:17][O:18][CH3:19])[N:12]=[C:11]2[C:7]=1[N:8]=[C:9](Br)[N:10]2[CH2:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1>CO.C(COC)OC>[NH2:5][C:6]1[N:14]=[C:13]([O:15][CH2:16][CH2:17][O:18][CH3:19])[N:12]=[C:11]2[C:7]=1[N:8]=[C:9]([O:2][CH3:1])[N:10]2[CH2:20][C:21]1[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 58019866HCID 58019866, compound

Product 1

HCID 58019861HCID 58019861, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
100 °C

Procedure

Sodium methoxide is generated by reaction of sodium metal (81 mg) in dry methanol (30 mL). The product of example 4 (700 mg) is dissolved in dry dimethoxyethane and the temperature raised to 100° C. After overnight reaction, the mixture is concentrated in vacuo and the residue is chromatographed on silica using 5% methanol in dichloromethane. Yield 120 mg. NMR is consistent with structure assignment.

Workup

  1. customAfter overnight reaction
  2. concentrationthe mixture is concentrated in vacuo
  3. customthe residue is chromatographed on silica using 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-db990e5aa4d24bf1be0b5ae186e43d3f
Source dataset
uspto-grants-2016_06
Patent number
US09359360B2

Reaction notes

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