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

HRID 271514노트

반응식

HRID 271514 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-98a5e996fa7a46de8b85200e8537352c
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452906B2

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