Potassium Carbonate → tert-butyl 4-(3-amino-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 2115885Notes

Reaction equation

HRID 2115885 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:12])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CC1(C)C(C)(C)OB([C:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH:22]=2)O1.C(=O)([O-])[O-].[K+].[K+]>ClC1C=C[C-](P(C2C=CC=CC=2)C2C=CC=CC=2)C=1Cl.[CH-]1C=CC=C1.[Fe+2].[Pd].CN(C=O)C>[NH2:12][C:4]1[CH:3]=[C:2]([C:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH:22]=2)[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27358803-Bromo-5-(trifluoromethyl)anilineHCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate

Product 1

HCID 67520234tert-butyl 4-(3-amino-5-(trifluoromethyl)phenyl)-5,6-dihydropyridine-1(2H)-carboxylate

Reagents, catalysts & solvents 2

HCID 178478231HCID 178478231, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

Into a 50 mL round bottom flask was placed 3-bromo-5-(trifluoromethyl)benzenamine (1 g, 4.16 mmol) and DMF (10 mL). To this was added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.67 g, 5.4 mmol), palladium dichlorodiphenylphosphinoferrocene (183 mg, 0.24 mmol), potassium carbonate (2.29 g, 16.6 mmol). Allowed to heat at 80° C. with stirring for 20 h. Work up: Reaction cooled to RT, solvents removed under reduced pressure. Purified via silica column using 0 to 8% MeOH gradient in DCM. Best fractions pooled, solvents removed under reduced pressure. Affords a clear oil. LC-MS(+) shows mass 343 (M+H) as expected for C17H21F3N2O2, mw 342.36.

Workup

  1. customInto a 50 mL round bottom flask was placed
  2. customReaction
  3. temperaturecooled to RT
  4. customsolvents removed under reduced pressure
  5. customPurified via silica column
  6. customsolvents removed under reduced pressure
  7. customAffords a clear oil

Sources & evidence

ORD record
ord-82ee11fc48fc428dbf59cebc7a864f98
Source dataset
uspto-grants-2008_10
Patent number
US07435823B2

Reaction notes

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