Cesium carbonate → HCID 71062756, compound

HRID 593302Notes

Reaction equation

HRID 593302 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=[O:12])[CH2:6][CH2:5]2.C(=O)([O-])[O-].[Cs+].[Cs+].[N+:19]([C:22]1[CH:27]=[CH:26][C:25](B(O)O)=[CH:24][CH:23]=1)([O-:21])=[O:20]>O1CCOCC1.O.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>[N+:19]([C:22]1[CH:27]=[CH:26][C:25]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[CH2:8][C:7](=[O:12])[CH2:6][CH2:5]3)=[CH:24][CH:23]=1)([O-:21])=[O:20]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27335536-Bromo-2-tetraloneHCID 27735524-Nitrophenylboronic acid

Product 1

HCID 71062756HCID 71062756, compoundYield 50.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

Pd(PPh3)4 (0.0736 g, 0.06 mmol) was added to a solution of 6-bromo-2-tetralone (1.5 g, 6.66 mmol) in 50 mL of 1,4 dioxane-H2O (3:1) mixture under argon atmosphere, followed by cesium carbonate (6.49 g, 19.99 mmol) and 4-nitrophenyl boronic acid (1.32 g, 7.99 mmol). The reaction mixture was degassed for 5 min. The reaction mixture was refluxed for 4 h and solvent removed under reduced pressure. The residue partitioned between ethyl acetate and water. The separated organic layer was dried over sodium sulphate, filtered and removed under reduced pressure. The product was purified by flash chromatography using 18% ethyl acetate in hexane to afford title compound (0.9 g, 50%) as solid. 1H NMR (300 MHz, CDCl3): 8.31 (d, J=9.0 Hz, 2H), 7.74 (d, J=8.4 Hz, 2H), 7.5 (m, 2H), 7.27 (s, 1H), 3.66 (s, 2H), 3.16 (t, J=6.9 Hz, 2H), 2.61 (t, J=6.9 Hz, 2H).

Workup

  1. customThe reaction mixture was degassed for 5 min
  2. temperatureThe reaction mixture was refluxed for 4 h
  3. customsolvent removed under reduced pressure
  4. customThe residue partitioned between ethyl acetate and water
  5. dry with materialThe separated organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. customremoved under reduced pressure
  8. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-9fecf12a6f7b44dc91712351ac3d27e1
Source dataset
uspto-grants-2016_01
Patent number
US09242929B2

Reaction notes

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