Sodium Carbonate → HCID 89543977, compound

HRID 922792Notes

Reaction equation

HRID 922792 reaction equation
Br[C:2]1[C:11]2[C:6](=[C:7]([F:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:13]([O:15]C)=[O:14])[CH:3]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1.C([O-])([O-])=O.[Na+].[Na+].C(=O)([O-])O.[Na+]>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.O1CCOCC1>[F:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([C:13]([OH:15])=[O:14])[CH:3]=[C:2]2[C:21]1[CH:22]=[CH:23][C:18]([F:17])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 516892Sodium BicarbonateHCID 60209919HCID 60209919, compound

Product 1

HCID 89543977HCID 89543977, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

Methyl 4-bromo-8-fluoroquinoline-2-carboxylate (7-3, 100.0 mg, 0.352 mmol), 4-Fluorophenylboronic acid (59.1 g, 0.422 mmol), Tetrakis (20.3 mg, 0.0180 mmol), and Na2CO3 (0.704 ml, 0.704 mmol) were added into 1,4-Dioxane (1.0 mL) in a microwave reaction vessel. The mixture was irradiated with microwave at 100° C. for 30 min. Cooled to room temperature, aqueous Sodium Hydrogen Carbonate (saturate, 2.0 mL) was added and extracted with Ethyl Acetate (2×10.0 mL). The combined organic fractions were washed with brine, dried over MgSO4, filtered and the solvent was evaporated under reduced pressure to give 8-Fluoro-4-(4-fluorophenyl)quinoline-2-carboxylic acid (7-4, 100.0 mg, 100.0% crude). LRMS m/z (M+H)+ 286.2 found, 286.2 required.

Workup

  1. customThe mixture was irradiated with microwave at 100° C. for 30 min
  2. extractionextracted with Ethyl Acetate (2×10.0 mL)
  3. washThe combined organic fractions were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-86ee2f559a2d4245aa3d7f7b60babfdf
Source dataset
uspto-grants-2016_03
Patent number
US09278960B2

Reaction notes

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