Potassium Carbonate → HCID 86687527, compound

HRID 1473478Notes

Reaction equation

HRID 1473478 reaction equation
Cl.Cl[C:3]1[C:12]2[C:7](=[CH:8][C:9]([Cl:13])=[CH:10][CH:11]=2)[N:6]=[N:5][CH:4]=1.[CH3:14][O:15][C:16]1[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[CH:18][C:17]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[Cl:13][C:9]1[CH:8]=[C:7]2[C:12]([C:3]([C:17]3[CH:18]=[CH:19][C:20]([C:22]([F:25])([F:24])[F:23])=[CH:21][C:16]=3[O:15][CH3:14])=[CH:4][N:5]=[N:6]2)=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 24901776(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acidHCID 86687528HCID 86687528, compound

Product 1

HCID 86687527HCID 86687527, compoundYield 36.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A microwave vial charged with 4,7-dichlorocinnoline hydrochloride (HDH Pharma, Morrisville, N.C.) (0.400 g, 1.7 mmol), 2-methoxy-4-(trifluoromethyl)phenylboronic acid (Combi-Blocks, San Diego, Calif.) (0.513 g, 1.7 mmol), potassium carbonate (1.172 g, 8.49 mmol), dioxane (6.36 ml) and water (2.1 ml); the system was purged with argon prior to the addition of Pd(PPh3)4 (0.196 g, 0.168 mmol). The mixture was irradiated for 30 min at 100° C. The organic layer was decanted and the aqueous phase was rinsed once with EtOAc. The combined organics were dried under reduced pressure and purified with a 40 g silicycle HP column (SiliCycle, Inc. Quebec City, Canada) ramping EtOAc in heptane (0 to 35%, 10% DCM throughout) providing 7-chloro-4-(2-methoxy-4-(trifluoromethyl)phenyl)cinnoline (0.212 g, 0.626 mmol, 36.8% yield) as a light yellow solid. m/z (ESI) 339.2 (M+H)+.

Workup

  1. customthe system was purged with argon
  2. customThe mixture was irradiated for 30 min at 100° C
  3. customThe organic layer was decanted
  4. washthe aqueous phase was rinsed once with EtOAc
  5. customThe combined organics were dried under reduced pressure
  6. custompurified with a 40 g silicycle HP column (SiliCycle, Inc. Quebec City, Canada)

Sources & evidence

ORD record
ord-458d2fdeb8ad4055ae0a750b60d83aec
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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