Cesium carbonate → HCID 178424207, compound

HRID 2383484Notes

Reaction equation

HRID 2383484 reaction equation
Br[C:2]1[C:14]2[C:13]3[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=3[CH:7]=[N:6][C:5]=2[NH:4][N:3]=1.[C:22]1([CH3:31])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C(O)C>[C:22]1([CH3:31])[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:2]1[C:14]2[C:13]3[CH2:12][CH2:11][N:10]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:9][C:8]=3[CH:7]=[N:6][C:5]=2[NH:4][N:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27332672-Methylphenyl boronic acidHCID 178451611HCID 178451611, compound

Product 1

HCID 178424207HCID 178424207, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

To 77 mM solution of tert-butyl 1-bromo-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate (1.3 mL) in toluene and absolute ethanol (2:1) was added o-tolylboronic acid (0.0136 g, 0.1 mmol) followed by 1M solution of cesium carbonate (0.6 mL) and 1,1-bis(Di-tBuppf)PdCl2 (0.005 g). The reaction mixture was shaken at 110° C. for 24 hours. On completion of the reaction, the reaction mixture was extracted with EtOAc (2×2 mL). The organic layers were combined and concentrated under reduced pressure to give the desired crude product, tert-butyl 1-o-tolyl-8,9-dihydro-3H-pyrazolo[3,4-c][2,7]naphthyridine-7(6H)-carboxylate as an brown solid, which was used in the next step without any further purification.

Workup

  1. customOn completion of the reaction
  2. extractionthe reaction mixture was extracted with EtOAc (2×2 mL)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac4ccd7175724cb48140eafab6f67ee8
Source dataset
uspto-grants-2012_09
Patent number
US08263610B2

Reaction notes

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