Sodium Carbonate → HCID 10314804, compound

HRID 425922Notes

Reaction equation

HRID 425922 reaction equation
C(OC([N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[C:13]1[CH:14]=[N:15][C:16]([NH2:29])=[C:17]([O:19][CH2:20][C:21]2[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:28])[CH:18]=1)=O)(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>C(O)C.O>[Cl:27][C:26]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:28])[C:21]=1[CH2:20][O:19][C:17]1[C:16]([NH2:29])=[N:15][CH:14]=[C:13]([C:9]2[NH:8][CH:12]=[CH:11][CH:10]=2)[CH:18]=1

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 10388186HCID 10388186, compound

Product 1

HCID 10314804HCID 10314804, compound

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

To a mixture of 2-[6-amino-5-(2,6-dichloro-benzyloxy)-pyridin-3-yl]-pyrrole-1-carboxylic acid tert-butyl ester (Example 6, 30 mg, 0.069 mmol) in ethanol/water (2:1, 10 mL) was added sodium carbonate (100 mg, 0.95 mmol). The mixture was refluxed overnight. The reaction was cooled to ambient temperature and extracted with ethyl acetate. The mixture was washed with water, brine, dried over Na2SO4, and purified on a silica gel column to afford 3-(2,6-dichloro-benzyloxy)-5-(1H-pyrrol-2-yl)-pyridin-2-ylamine.

Workup

  1. temperatureThe mixture was refluxed overnight
  2. extractionextracted with ethyl acetate
  3. washThe mixture was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. custompurified on a silica gel column

Sources & evidence

ORD record
ord-4ccffa91deca46d6ab0e9f117c699146
Source dataset
uspto-grants-2012_01
Patent number
US08106197B2

Reaction notes

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