Potassium tert-butoxide → 6-(5-Chloro-1,8-naphthyridin-2-yl)-5-(trifluoromethyl)pyridin-3-amine

HRID 545066Notes

Reaction equation

HRID 545066 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:3]=1[CH:4]=O.[C:11]([C:14]1[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][C:17]([NH2:24])=[CH:16][N:15]=1)(=O)[CH3:12].CC([O-])(C)C.[K+]>C1COCC1>[Cl:10][C:6]1[CH:7]=[CH:8][N:9]=[C:2]2[C:3]=1[CH:4]=[CH:12][C:11]([C:14]1[N:15]=[CH:16][C:17]([NH2:24])=[CH:18][C:19]=1[C:20]([F:23])([F:21])[F:22])=[N:1]2

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 462035412-Amino-4-chloropyridine-3-carbaldehydeHCID 586455412-Acetyl-5-amino-3-trifluoromethylpyridine

Product 1

HCID 586456816-(5-Chloro-1,8-naphthyridin-2-yl)-5-(trifluoromethyl)pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

Dissolve 2-amino-4-chloronicotinaldehyde (78 mg, 0.5 mmol) and 2-acetyl-5-amino-3-trifluoromethylpyridine (102 mg, 0.5 mmol) in anhydrous THF (5.0 mL) and cool it to −40° C. under N2 atmosphere. Add in portion t-BuOK (112 mg, 1.0 mmol) to the reaction mixture and stir the mixture at −110° C. for 2 hours. Concentrate the reaction mixture under vacuum, dilute the residue with water (20 mL), extract with CH2Cl2 (3×30 mL) and dry (MgSO4). Filter, concentrate under vacuum and purify the crude by column chromatography to afford the title compound product as a yellow solid.

Workup

  1. concentrationConcentrate the reaction mixture under vacuum
  2. additiondilute the residue with water (20 mL)
  3. extractionextract with CH2Cl2 (3×30 mL)
  4. dry with materialdry (MgSO4)
  5. filtrationFilter
  6. concentrationconcentrate under vacuum
  7. custompurify the crude by column chromatography

Sources & evidence

ORD record
ord-d9fec453608148ffaf01a09c70465814
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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