Potassium Carbonate → HCID 68294895, compound

HRID 1909342Notes

Reaction equation

HRID 1909342 reaction equation
Br[C:2]1[CH:3]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[C:5]2[CH:6]=[N:7][N:8]([CH:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:9]=2[CH:10]=1.[C:20]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C([O-])([O-])=O.[K+].[K+].N1CCC[C@H]1C(O)=O>CS(C)=O.[Cu]I.O>[C:23]([O:22][C:20]([N:27]1[CH2:32][CH2:31][N:30]([C:2]2[CH:3]=[C:4]([C:16]([O:18][CH3:19])=[O:17])[C:5]3[CH:6]=[N:7][N:8]([CH:11]4[CH2:15][CH2:14][CH2:13][CH2:12]4)[C:9]=3[CH:10]=2)[CH2:29][CH2:28]1)=[O:21])([CH3:26])([CH3:24])[CH3:25]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 143452tert-Butyl piperazine-1-carboxylateHCID 145742L-ProlineHCID 67468180Methyl 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylate

Product 1

HCID 68294895HCID 68294895, compoundYield 30.1%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of methyl 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylate (5 g, 15.527 mmol) in DMSO (25 mL), 1-Boc piperazine (4.3 g, 23.3 mmol), K2CO3 (4.28 g, 31.05 mmol), CuI (0.295 g, 1.55 mmol) and L-proline (0.357 g, 3.1 mmol) were added in given order and resulting reaction mixture heated to 100° C. for 48 h. On completion, the reaction mixture was poured into water and extracted with DCM. The combined organic layers were washed with water and dried over sodium sulfate. The solvent was removed under reduced pressure to obtain crude residue which was purified by column chromatography over silica gel affording methyl 6-(4-(tert-butoxycarbonyl)piperazin-1-yl)-1-cyclopentyl-1H-indazole-4-carboxylate (2 g, 30%).

Workup

  1. customresulting
  2. customreaction mixture
  3. extractionextracted with DCM
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customto obtain crude residue which
  8. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-de9d873436524be793af61317d4ba028
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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