4-Bromoindan-1-one O-methyloxime → 4-Pyridin-2-yl-indan-1-one O-methyl-oxime

HRID 451631Notes

Reaction equation

[Br-].[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Zn+].[CH3:9][O:10][N:11]=[C:12]1[C:20]2[C:15](=[C:16](Br)[CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1>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>[CH3:9][O:10][N:11]=[C:12]1[C:20]2[C:15](=[C:16]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=3)[CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13]1

Participants

Conditions

Temperature: 120 °C

Procedure

2-Pyridylzinc bromide (10 mL, 5 mmol, 0.5M in THF) was added to 4-bromoindan-1-one O-methyl-oxime (600 mg, 2.5 mmol) and Pd(PPh3)4 (58 mg, 0.05 mmol) under nitrogen atmosphere. The stirred solution was heated at 120° C. for 10 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 20-40% ethyl acetate in hexane. Obtained 4-pyridin-2-ylindan-1-one O-methyloxime (326 mg, 55%) as a yellow oil. MS (DCI/NH3) m/z: 239.09 [M+H]+. 1H NMR (DMSO-d6) δ: 2.82 (m, 2H), 3.29 (m, 2H), 3.92 (s, 3H), 7.36 & 7.38 (pair of dd, 1H), 7.43 (t, 1H), 7.64 (dd, 1H), 7.74 (dd, 1H), 7.75 (dt, 1H), 7.91 (td, 1H), 8.68 & 8.69 (pair of dd, 1H).

Workup

temperatureAfter cooling to ambient temperature
filtrationthe reaction mixture was filtered through celite
concentrationThe filtrate was concentrated to a brown oil
customchromatographed on silica gel with 20-40% ethyl acetate in hexane

Sources & evidence

ORD record: ord-6814c353495e4789ae9fb8b8167e2649
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487116B2

Reaction notes

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