Dichloromethane → N-[6-(Isoquinolin-5-yl)naphthalen-2-yl]-4-methoxybenzamide

HRID 908317Notes

Reaction equation

HRID 908317 reaction equation
FC(F)(F)S(O[C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([NH:17][C:18](=[O:27])[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:13]=2)[CH:8]=1)(=O)=O.[CH:30]1[C:39]2[C:34](=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][N:31]=1.C(=O)([O-])[O-].[K+].[K+].C(Cl)Cl>O1CCOCC1.O>[CH:30]1[C:39]2[C:34](=[C:35]([C:7]3[CH:8]=[C:9]4[C:14](=[CH:15][CH:16]=3)[CH:13]=[C:12]([NH:17][C:18](=[O:27])[C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH:11]=[CH:10]4)[CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][N:31]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 599474Isoquinoline-5-boronic acidHCID 86761407HCID 86761407, compound

Product 1

HCID 58828879N-[6-(Isoquinolin-5-yl)naphthalen-2-yl]-4-methoxybenzamideYield 3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a microwave vial containing 6-(4-methoxybenzamido)naphthalen-2-yl trifluoromethanesulfonate (0.100 g, 0.2 mmol), in 1,4-Dioxane (3 mL), was added isoquinolin-5-ylboronic acid (0.129 g, 0.8 mmol), Fibrecat catalyst (0.005 g, 5% by wt.), 2 M Potassium Carbonate (0.50 mL, 1 mmol). The vial was capped and placed into CEM Microwave for 10 minutes at 80° C., while supplying 50 Watts of power through power-max. The diluted the mixture [with DCM (2 mL) and water (2 mL)] was extracted with DCM (3×10 mL). The dried organics (over sodium sulfate) was filtered, and concentrated in-vacuo. The crude was purified from reverse-phase HPLC. This gave a tan colored amorphous solid, which was titled product (0.0023 g, 0.006 mmol) MS (ESI pos. ion) m/z: 405 (M+H). Calc'd Exact Mass for C27H20N2O2: 404.

Workup

  1. customThe vial was capped
  2. extractionwas extracted with DCM (3×10 mL)
  3. filtrationThe dried organics (over sodium sulfate) was filtered
  4. concentrationconcentrated in-vacuo
  5. customThe crude was purified from reverse-phase HPLC
  6. customThis gave a tan colored amorphous solid, which

Sources & evidence

ORD record
ord-969761393054401cb8f98c06bf38fd4a
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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