Potassium Carbonate → 4-Bromo-5-(1-methoxyimino-indan-5-yl)-furan-2-carbaldehyde

HRID 271514Notes

Reaction equation

HRID 271514 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[O:9])[O:5][C:6]=1Br.[CH3:10][O:11][N:12]=[C:13]1[C:21]2[C:16](=[CH:17][C:18](B(O)O)=[CH:19][CH:20]=2)[CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[O:9])[O:5][C:6]=1[C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[C:13](=[N:12][O:11][CH3:10])[CH2:14][CH2:15]2

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 10852284,5-Dibromofuran-2-carbaldehydeHCID 734146811-Methoxyimino-indan-5-boronic acid

Product 1

HCID 867607594-Bromo-5-(1-methoxyimino-indan-5-yl)-furan-2-carbaldehydeYield 35.2%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A degassed mixture of the product of Step 3 (6.6 g, 26.0 mmol), 1-methoxyimino-indan-5-boronic acid (5.3 g, 26.0 mmol) and potasium carbonate (28 g, 202 mmol) in ethylene glycol dimethyl ether (150 ml) and water (75 ml) was treated with bis(triphenylphosphine) palladium (II) chloride (1.05 g, 1.5 mmol), then heated under reflux for 6 hours. After cooling to room temperature, the mixture was filtered through celite and the filtrate diluted with water and ethyl acetate. The organic phase was separated, washed with water and brine, dried, concentrated in vacuo and the residue purified by silica gel chromatography eluting with dichloromethane to give the title compound (3.06 g, 35%); MS(ES+) m/e 334/336 [M+H]+.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 6 hours
  3. filtrationthe mixture was filtered through celite
  4. additionthe filtrate diluted with water and ethyl acetate
  5. customThe organic phase was separated
  6. washwashed with water and brine
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customthe residue purified by silica gel chromatography
  10. washeluting with dichloromethane

Sources & evidence

ORD record
ord-98a5e996fa7a46de8b85200e8537352c
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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