Potassium Carbonate → N-(6-(isoquinolin-5-yl)naphthalen-2-yl)thiophene-2-carboxamide

HRID 908310Notes

Reaction equation

HRID 908310 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]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[O:19])[CH:13]=2)[CH:8]=1)(=O)=O.[CH:27]1[C:36]2[C:31](=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][N:28]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C(Cl)Cl.O>[CH:27]1[C:36]2[C:31](=[C:32]([C:7]3[CH:8]=[C:9]4[C:14](=[CH:15][CH:16]=3)[CH:13]=[C:12]([NH:17][C:18]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=3)=[O:19])[CH:11]=[CH:10]4)[CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][N:28]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 599474Isoquinoline-5-boronic acidHCID 866112546-(Thiophene-2-carboxamido)naphthalen-2-yl trifluoromethanesulfonate

Product 1

HCID 11990812N-(6-(isoquinolin-5-yl)naphthalen-2-yl)thiophene-2-carboxamideYield 100%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a microwave vial containing 6-(thiophene-2-carboxamido)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.), and Potassium Carbonate (2 M, 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 mixture was diluted with DCM (2 mL) and water (2 mL). The aqueous layer was extracted with DCM (3×10 mL). The combined organics was dried over sodium sulfate, filtered, and concentrated in-vacuo. The crude was purified from reverse-phase HPLC. This gave a yellow colored amorphous solid, which was titled product (0.078 g, 0.2 mmol). MS (ESI pos. ion) m/z: 381 (M+H).

Workup

  1. customThe vial was capped
  2. extractionThe aqueous layer was extracted with DCM (3×10 mL)
  3. dry with materialThe combined organics was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in-vacuo
  6. customThe crude was purified from reverse-phase HPLC
  7. customThis gave a yellow colored amorphous solid, which

Sources & evidence

ORD record
ord-6bb87cdc355741958849ce96103e7dcb
Source dataset
uspto-grants-2011_09
Patent number
US08017601B2

Reaction notes

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