Tetrahydrofuran → HCID 67416078, compound

HRID 2192992Notes

Reaction equation

HRID 2192992 reaction equation
Cl[C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[C:6](Cl)=[N:7]2.C(OC([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](B(O)O)=[CH:26]1)=O)(C)(C)C.C1C[O:40]CC1>C([O-])([O-])=O.[Na+].[Na+]>[F:17][C:15]1[CH:14]=[CH:13][C:5]2[C:6]([C:27]3[C:28]4[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=4)[NH:25][CH:26]=3)=[N:7][C:8]3[CH:9]=[CH:10][NH:11][C:2](=[O:40])[C:3]=3[C:4]=2[CH:16]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 52330101-(tert-Butoxycarbonyl)indole-3-boronic acidHCID 59375375HCID 59375375, compound

Product 1

HCID 67416078HCID 67416078, compound

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 1,6-dichloro-9-fluorobenzo[c]-1,6-naphthyridine (20 mg, 0.075 mmol) in THF (2 mL) and 2.0 M Na2CO3 (500 μL) were added [1-(tert-butoxycarbonyl)-1H-indol-3-yl]boronic acid (23.5 mg, 0.09 mmol). The solution was degassed by bubbling N2 for 5 min heated to 150° C. for 1 hr in a microwave reactor. The reaction solution was extracted with EtOAc and water, the organic layers were dried with MgSO4, filtered, and concentrated by rotary evaporation. Silcia gel column chromatography with 100% CH2Cl2 to 25% MeOH provided the 9-fluoro-6-(1H-indol-3-yl)benzo[c]-1,6-naphthyridin-1(2H)-one. LRMS (ESI) calc'd for (C20H13FN3O) [M+H]+, 330.1; found 330.1

Workup

  1. customThe solution was degassed
  2. customby bubbling N2 for 5 min
  3. extractionThe reaction solution was extracted with EtOAc and water
  4. dry with materialthe organic layers were dried with MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-a9fb2cca65cf4a3691ae162e141238ab
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

Loading…