Potassium Carbonate → HCID 131728130, compound

HRID 2238682Notes

Reaction equation

HRID 2238682 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH2:10][CH2:11][N:12]([C:15](=[O:20])[C:16]([F:19])([F:18])[F:17])[CH2:13][CH:14]=2)O1.[C:22]([O:26][C:27](=[O:38])[NH:28][C@H:29]([C:31]1[CH:36]=[CH:35][C:34](Br)=[CH:33][CH:32]=1)[CH3:30])([CH3:25])([CH3:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:22]([O:26][C:27](=[O:38])[NH:28][C@H:29]([C:31]1[CH:32]=[CH:33][C:34]([C:9]2[CH2:10][CH2:11][N:12]([C:15](=[O:20])[C:16]([F:17])([F:18])[F:19])[CH2:13][CH:14]=2)=[CH:35][CH:36]=1)[CH3:30])([CH3:23])([CH3:24])[CH3:25]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 56973617(S)-tert-Butyl (1-(4-bromophenyl)ethyl)carbamateHCID 713023762,2,2-Trifluoro-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridin-1(2H)-yl]ethan-1-one

Product 1

HCID 131728130HCID 131728130, compoundYield 38.4%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

400 mg of the 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(trifluoroacetyl)-1,2,3,6-tetrahydropyridine [154-2] was dissolved in 10 mL of N,N-dimethylformamide, then 196 mg of the t-butyl[(1S)-1-(4-bromophenyl)ethyl]carbamate [106-1], 54 mg of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II), and 181 mg of potassium carbonate were added thereto, and stirred overnight at 80° C. The reaction mixture was cooled back to room temperature, then diluted in 100 mL of ethyl acetate, and washed with water and saturated brine in the subsequent order. The obtained organic layer was dried over anhydrous magnesium sulfate, and the insolubles were filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography, to obtain 100 mg of t-butyl((1S)-1-{4-[1-(trifluoroacetyl)-1,2,3,6-tetrahydropyridin-4-yl]phenyl}ethyl)carbamate [154-3] as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled back to room temperature
  2. washwashed with water and saturated brine in the subsequent order
  3. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  4. filtrationthe insolubles were filtered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-743e3e379bbb4b71851eb4845ed4a9ce
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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