Cesium carbonate → HCID 86719547, compound

HRID 2208762Notes

Reaction equation

HRID 2208762 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:13]([CH:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH3:14])[C:5]([CH3:12])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].[N:20]1([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].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>[CH:15]1([N:13]([CH3:14])[C:4]2[CH:3]=[C:2]([N:23]3[CH2:22][CH2:21][N:20]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:25][CH2:24]3)[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=2[CH3:12])[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 70872667HCID 70872667, compound

Product 1

HCID 86719547HCID 86719547, compoundYield 33.3%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of methyl 5-bromo-3-(cyclopentyl(methyl)amino)-2-methylbenzoate (1 g, 3.07 mmol), tert-butyl piperazine-1-carboxylate (0.85 g, 4.61 mmol) and Cs2CO3 (0.5 g, 1.53 mmol) in toluene (25 mL) was purged with argon for 10 min. Then, Pd2(dba)3 (0.31 g, 0.307 mmol) and BINAP (0.038 g, 0.061 mmol) was added to it and argon purged again for 10 min. The reaction mixture was stirred at 100° C. for 8 h. After completion, water was added to it and extracted with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material which was purified by column chromatography to afford the title compound (0.44 g, 33.3%).

Workup

  1. custompurged again for 10 min
  2. additionAfter completion, water was added to it
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto afford crude material which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-6938e1a9fc994ae697777b7ce62fe3e5
Source dataset
uspto-grants-2016_06
Patent number
US09376422B2

Reaction notes

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