Cesium carbonate → HCID 67513426, compound

HRID 1508527Notes

Reaction equation

HRID 1508527 reaction equation
Cl[C:2]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][N:3]=1.[F:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl.C1COCC1>[F:16][C:17]1[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[CH:19][C:18]=1[C:2]1[N:3]=[CH:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2775340Methyl 6-chloro-4-(trifluoromethyl)nicotinateHCID 15789384(2-Fluoro-4-methoxyphenyl)boronic acid

Product 1

HCID 67513426HCID 67513426, compound

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 6-chloro-4-(trifluoromethyl)nicotinate (963.6 mg, 4.02 mmol), 2-fluoro-4-methoxybenzeneboronic acid (854 mg, 5.03 mmol), cesium carbonate (2883 mg, 8.85 mmol), PdCl2(dppf)-CH2Cl2 adduct (328 mg, 0.402 mmol) and THF (30 mL) were refluxed in a 80° C. oil bath overnight. LCMS trace of the reaction aliquot indicated completion of reaction. The reaction crude was filtered through a bed of Celite® 521. The filtrate was concentrated in vacuo and purified by flash chromatography (SiO2, Biotage SNAP Cartridge, silica gel, KP-Sil, 100 g cartridge). The column was eluted by an EtOAc/hexanes mixture (0% to 20%). Related fractions were pooled and evaporated to afford a colorless oil as the titled compound. LCMS calc.=329.07. found=330.17 (M+H)+.

Workup

  1. customLCMS trace of the reaction aliquot indicated completion of reaction
  2. customThe reaction crude
  3. filtrationwas filtered through a bed of Celite® 521
  4. concentrationThe filtrate was concentrated in vacuo
  5. custompurified by flash chromatography (SiO2, Biotage SNAP Cartridge, silica gel, KP-Sil, 100 g cartridge)
  6. washThe column was eluted by an EtOAc/hexanes mixture (0% to 20%)
  7. customevaporated

Sources & evidence

ORD record
ord-a50dcd064cd742adb5ef4767578712f6
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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