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Potassium Carbonate → 3,5-Dichloro-2-fluoro-4-(3-isopropyl-4-methoxyphenoxy)-6-methoxycarbonylmethylamino-pyridine

HRID 352541
Notes
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Reaction equation

HRID 352541 reaction equation
[Cl:1][C:2]1[C:3](F)=[N:4][C:5]([F:21])=[C:6]([Cl:20])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1.Cl.[CH3:24][O:25][C:26](=[O:29])[CH2:27][NH2:28].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Cl-].[Na+].O>[Cl:20][C:6]1[C:5]([F:21])=[N:4][C:3]([NH:28][CH2:27][C:26]([O:25][CH3:24])=[O:29])=[C:2]([Cl:1])[C:7]=1[O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[C:11]([CH:17]([CH3:19])[CH3:18])[CH:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 122755Glycine methyl ester hydrochlorideHCID 227120853,5-Dichloro-2,6-difluoro-4-(3-isopropyl-4-methoxyphenoxy)pyridine

Product 1

HCID 98881843,5-Dichloro-2-fluoro-4-(3-isopropyl-4-methoxyphenoxy)-6-methoxycarbonylmethylamino-pyridineYield 62%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3,5-dichloro-2,6-difluoro-4-(3-isopropyl-4-methoxyphenoxy)pyridine. (584 mg) and glycine methyl ester hydrochloric acid (220 mg) in DMF (5.0 mL) was added potassium carbonate powder (500 mg) in one portion. The resulting mixture was stirred at ambient temperature for 20 hours. The reaction mixture was diluted with brine, extracted with ethyl acetate (50 mL×2). The combined organic layers were washed with brine (50 mL×3), dried (Na2SO4), and concentrated. Chromatography with ethyl acetate-hexanes (0-50% gradient elution) afforded the title compound as a colorless oil (434 mg, 62%).

Workup

  1. extractionextracted with ethyl acetate (50 mL×2)
  2. washThe combined organic layers were washed with brine (50 mL×3)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d849c29223244e9db6b6dfd96411e60c
Source dataset
uspto-grants-2004_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06747048B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes