Dichloromethane → 4-Pyridin-3-yl-indan-1-one O-methyl-oxime

HRID 451630Notes

Reaction equation

HRID 451630 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[C:8](Br)[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16](B(O)O)[CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].C(Cl)Cl>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].O.CCO.COCCOC>[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[C:8]([C:16]3[CH:15]=[N:14][CH:19]=[CH:18][CH:17]=3)[CH:9]=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

Participants

9

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 766564474-Bromoindan-1-one O-methyloxime

Product 1

HCID 860167824-Pyridin-3-yl-indan-1-one O-methyl-oxime

Reagents, catalysts & solvents 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
160 °C

Procedure

4-Bromoindan-1-one O-methyloxime (720 mg, 3.0 mmol) was added to a mixture of pyridine-3-boronic acid (406 mg, 3.3 mmol), sodium carbonate (477 mg, 4.5 mmol) and Pd(dppf)Cl2.CH2Cl2 (122 mg, 0.15 mmol) in 7:2:3 DME:EtOH:H2O (15 mL). The stirred mixture was heated at 160° C. for 3 minutes on the microwave. After cooling to ambient temperature, the reaction mixture was filtered through celite, then silica gel with ethyl acetate. The filtrate was concentrated to a brown oil and chromatographed on silica gel with 70% ethyl acetate in hexane. Obtained 4-pyridin-3-yl-indan-1-one O-methyloxime (667 mg, 93%) as a yellow oil. MS (ESI) m/z: 239.1 [M+H]+. 1H NMR (DMSO-d6) δ: 2.81 (m, 2H), 3.08 (m, 2H), 3.92 (s, 3H), 7.45 (m, 2H), 7.48 & 7.51 (pair of dd, 1H), 7.63 (dd, 1H), 7.94 & 7.97 (pair of dd, 1H), 8.60 (dd, 1H), 8.72 (dd, 1H).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. filtrationthe reaction mixture was filtered through celite
  3. concentrationThe filtrate was concentrated to a brown oil
  4. customchromatographed on silica gel with 70% ethyl acetate in hexane

Sources & evidence

ORD record
ord-12d0410efb43418d880bd433d6dbdbf3
Source dataset
uspto-grants-2013_07
Patent number
US08487116B2

Reaction notes

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