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Potassium Carbonate → Tert-butyl (2-oxo-1-(2-(trifluoromethyl)pyridin-4-yl)-1,2-dihydropyridin-4-yl)methylcarbamate

HRID 711264
Notes
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Reaction equation

HRID 711264 reaction equation
[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:5]=[CH:4][NH:3]1.C([O-])([O-])=O.[K+].[K+].Br[C:24]1[CH:29]=[CH:28][N:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1.CN[C@@H]1CCCC[C@H]1NC>C1(C)C=CC=CC=1.[Cu]I.C(OCC)(=O)C>[O:1]=[C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:15])[CH3:14])[CH:5]=[CH:4][N:3]1[C:24]1[CH:29]=[CH:28][N:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 234369504-Bromo-2-(trifluoromethyl)pyridineHCID 426256764-(Boc-aminomethyl)-1H-pyridin-2-one

Product 1

HCID 86679722Tert-butyl (2-oxo-1-(2-(trifluoromethyl)pyridin-4-yl)-1,2-dihydropyridin-4-yl)methylcarbamate

Reagents, catalysts & solvents

3
HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a reaction vessel containing a stir bar was charged with tert-butyl (2-oxo-1,2-dihydropyridin-4-yl)methylcarbamate 56-4 (72 mg, 0.32 mmol), CuI (12 mg, 0.06 mmol), and K2CO3 (88 mg, 0.64 mmol). The reaction vessel was evacuated and backfilled with nitrogen. A solution of 4-bromo-2-(trifluoromethyl)pyridine 56-5 (94 mg, 0.42 mmol) and (1R,2R)—N1,N2-dimethylcyclohexane-1,2-diamine (9 mg, 0.06 mmol) in toluene (3 mL) was added via syringe. The reaction was stirred at room temperature for 20 minutes, then 110° C. overnight. The reaction mixture was diluted into ethyl acetate and filtered through celite pad to remove salt. The filtrate was dried and the residue was purified by silica gel flash chromatography, and eluted with 50% ethyl acetate to give tert-butyl (2-oxo-1-(2-(trifluoromethyl)pyridin-4-yl)-1,2-dihydropyridin-4-yl)methylcarbamate 56-6. MS m/z 370.2 (M+1).

Workup

  1. additionTo a reaction vessel containing a stir bar
  2. customThe reaction vessel was evacuated
  3. custom110° C. overnight
  4. filtrationfiltered through celite pad
  5. customto remove salt
  6. customThe filtrate was dried
  7. customthe residue was purified by silica gel flash chromatography
  8. washeluted with 50% ethyl acetate

Sources & evidence

ORD record
ord-da3c63718785472e9f72f994ddba510e
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181235B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes