tert-Butyl piperazine-1-carboxylate → HCID 131734739, compound

HRID 1775365Notes

Reaction equation

HRID 1775365 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([F:9])[N:3]=1.[N:10]1([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.CC(C)([O-])C.[Na+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>C1COCC1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:9][C:4]1[N:3]=[C:2]([N:13]2[CH2:12][CH2:11][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][CH2:14]2)[CH:7]=[C:6]([CH3:8])[CH:5]=1

Participants

8

Reactant 4

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 299193662-Bromo-6-fluoro-4-methylpyridine

Product 1

HCID 131734739HCID 131734739, compoundYield 61%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2-Bromo-6-fluoro-4-methylpyridine (380 mg, 2 mmol), tert-butyl piperazine-1-carboxylate (466 mg, 2.5 mmol), Pd2(DBA)3 (40 mg, 0.044 mmol), sodium tert-butoxide (317 mg, 3.3 mmol) and BINAP (80 mg, 0.032 mmol) were dissolved in anhydrous THF (6 ml) under argon and heated at 80° C. under microwave heating. The mixture was diluted with ethyl acetate, filtered, the filtrate was evaporated under reduced pressure. The residue was dissolved in DCM and filtered through a pad of silica. The silica was washed with a mixture of DCM and diethylether, the combined filtrates were concentrated under reduced pressure to yield 360 mg (1.22 mmol, yield 61%) MS (multi-mode) m/z=296.2 [M+1]+.

Workup

  1. temperatureheating
  2. filtrationfiltered
  3. customthe filtrate was evaporated under reduced pressure
  4. dissolutionThe residue was dissolved in DCM
  5. filtrationfiltered through a pad of silica
  6. washThe silica was washed with a mixture of DCM and diethylether
  7. concentrationthe combined filtrates were concentrated under reduced pressure
  8. customto yield 360 mg (1.22 mmol, yield 61%)

Sources & evidence

ORD record
ord-b8b9b54d82e24798a2deddd36105d752
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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