Methanol → HCID 90408979, compound

HRID 516585Notes

Reaction equation

HRID 516585 reaction equation
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=2)[N:5]=[C:4]([C:17]([O:19][CH3:20])=[O:18])[C:3]=1[CH:21]=[CH2:22].[C:23](=O)([O-])[O-].[K+].[K+].CO.COP(C(=[N+]=[N-])C(=O)C)(=O)OC>CCOCC>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]#[CH:23])=[CH:11][CH:10]=2)[N:5]=[C:4]([C:17]([O:19][CH3:20])=[O:18])[C:3]=1[CH:21]=[CH2:22]

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 90408697Methyl 4-amino-5-fluoro-6-(4-formylphenyl)-3-vinylpicolinateHCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 90408979HCID 90408979, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 20 mL reaction vial was added methyl 4-amino-5-fluoro-6-(4-formylphenyl)-3-vinylpicolinate (0.41 g, 1.365 mmol), potassium carbonate (0.377 g, 2.73 mmol) and MeOH (10 mL). Dimethyl(1-diazo-2-oxopropyl)phosphonate (0.315 g, 1.638 mmol) was added in one portion. After stirring for 4 h, the reaction mixture was diluted with Et2O (50 mL) and washed with a 5% solution of NaHCO3 (25 mL) The organic layer was dried over MgSO4 (5 g), filtered, and concentrated on a rotary evaporator. The resulting reside was purified using a Teledyne ISCO purification system with a gradient eluent system of CH2Cl2 and EtOAc to yield the title compound as a white solid (250 mg).

Workup

  1. customTo a 20 mL reaction
  2. washwashed with a 5% solution of NaHCO3 (25 mL) The organic layer
  3. dry with materialwas dried over MgSO4 (5 g)
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator
  6. customThe resulting reside was purified
  7. customa Teledyne ISCO purification system with a gradient eluent system of CH2Cl2 and EtOAc

Sources & evidence

ORD record
ord-f3c17f85d21f4434bf781536f01c5f40
Source dataset
uspto-grants-2015_08
Patent number
US09113629B2

Reaction notes

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