Cesium carbonate → HCID 67513886, compound

HRID 1508520Notes

Reaction equation

HRID 1508520 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH2:9])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[CH3:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][C:23]=1B1OC(C)(C)C(C)(C)O1)[C:17]([O:19][CH3:20])=[O:18].C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([C:23]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[CH3:13])=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11])=[CH2:9]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 110870242-Methyl-4-methoxycarbonylphenylboronic acid, pinacol esterHCID 151503814-Chloro-1-ethenyl-2-nitrobenzene

Product 1

HCID 67513886HCID 67513886, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloro-1-ethenyl-2-nitrobenzene (1.1406 g, 6.21 mmol), methyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (2.059 g, 7.46 mmol), 1,1bis(di-tert-butylphosphino)ferrocene palladium dichloride (0.422 g, 0.621 mmol), cesium carbonate (4.25 g, 13.05 mmol) and THF (30 mL) were heated in an 80° C. oil bath overnight. Volatiles were removed under reduced pressure. The pot residue was taken up by dichloromethane and filtered. The filtrate was concentrated in vacuo to afford a dark solid. The resulting solid was purified by flash chromatography (SiO2, Biotage SNAP cartridge, silica gel, 100 g cartridge). The column was eluted by an EtOAc/hexanes mixture (0% to 40%). Related fractions were pooled and evaporated a light orange solid as the titled compound. LCMS calc.=297.10. found=298.10 (M+H)+.

Workup

  1. customVolatiles were removed under reduced pressure
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto afford a dark solid
  5. customThe resulting solid was purified by flash chromatography (SiO2, Biotage SNAP cartridge, silica gel, 100 g cartridge)
  6. washThe column was eluted by an EtOAc/hexanes mixture (0% to 40%)
  7. customevaporated a light orange solid as the titled compound

Sources & evidence

ORD record
ord-f21a300043c64f8aa32182b5cf76dd63
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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