Cesium carbonate → HCID 44594454, compound

HRID 1912002Notes

Reaction equation

HRID 1912002 reaction equation
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][N:6]=[CH:7]2.[NH2:12][C@@H:13]1[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH:7]1[C:8]2[C:3](=[C:2]([NH:12][C@@H:13]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14]3)[CH:11]=[CH:10][CH:9]=2)[CH:4]=[CH:5][N:6]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 7364875-BromoisoquinolineHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidine

Product 1

HCID 44594454HCID 44594454, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

Into a 50 mL round bottom flask were added 5-bromoisoquinoline (1.12 g, 5.4 mmol), toluene (10 mL), (R)-tert-butyl 3-aminopyrrolidine-1-carboxylate (1.00 g, 5.4 mmol), palladium acetate (0.18 g, 0.8 mmol), rac-(±)-BINAP (0.500 g, 0.8 mmol), and cesium carbonate (2.80 g, 8.6 mmol). The vessel was evacuated, refilled with nitrogen and stirred at 80° C. for 12 h. The mixture was diluted with ethyl acetate (20 mL), washed with water (10 mL), and the organic phase was dried over MgSO4, filtered and evaporated to afford the title compound (1.00 g, 59%). This material was of sufficient quality to be used without further purification.

Workup

  1. customThe vessel was evacuated
  2. additionrefilled with nitrogen
  3. additionThe mixture was diluted with ethyl acetate (20 mL)
  4. washwashed with water (10 mL)
  5. dry with materialthe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-3a041bff6eac405a9acdf48adfb6ebe1
Source dataset
uspto-grants-2013_12
Patent number
US08604218B2

Reaction notes

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