Cesium carbonate → HCID 123316877, compound

HRID 514308Notes

Reaction equation

HRID 514308 reaction equation
Br[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:4](=[O:18])[C:3]=1[CH3:19].[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[C:30]([CH3:37])[CH:29]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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]>[CH2:20]([O:27][C:28]1[CH:33]=[CH:32][C:31]([C:2]2[N:7]([CH3:8])[C:6](=[O:9])[N:5]([CH2:10][O:11][CH2:12][CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])[C:4](=[O:18])[C:3]=2[CH3:19])=[C:30]([CH3:37])[CH:29]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27732454-Benzyloxy-2-methylphenylboronic acidHCID 123772393HCID 123772393, compound

Product 1

HCID 123316877HCID 123316877, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of C3 (10 g, 29 mmol), [4-(benzyloxy)-2-methylphenyl]boronic acid (10.4 g, 43.0 mmol) and cesium carbonate (28 g, 86 mmol) in 1,4-dioxane (400 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (2.2 g, 3.0 mmol). The reaction mixture was heated at reflux for 4 hours, then filtered. The filtrate was concentrated, and the residue was purified by silica gel chromatography (Gradient: 10% to 20% ethyl acetate in petroleum ether) to provide the product as a light yellow solid. Yield: 10 g, 21 mmol, 72%. 1H NMR (400 MHz, CDCl3) δ 7.34-7.49 (m, 5H), 7.00 (d, half of AB quartet, J=8.3 Hz, 1H), 6.91-6.97 (m, 2H), 5.50 (AB quartet, JAB=9.2 Hz, ΔνAB=4.1 Hz, 2H), 5.10 (s, 2H), 3.73-3.79 (m, 2H), 3.03 (s, 3H), 2.15 (s, 3H), 1.65 (s, 3H), 1.00-1.06 (m, 2H), 0.03 (s, 9H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 hours
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by silica gel chromatography (Gradient: 10% to 20% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-91008510e0d24ea39f7600d4dc83de9e
Source dataset
uspto-grants-2015_08
Patent number
US09107923B2

Reaction notes

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