Piperidine → 3-(3-Bromo-2-methylbenzylidene)indolin-2-one

HRID 661856Notes

Reaction equation

[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][C:12]1=[O:20].N1CCCCC1>C(O)C>[Br:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=[C:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:11][C:12]1=[O:20]

Participants

Conditions

Temperature: 82.5 °C

Procedure

Step 2 A solution of 3-bromo-2-methylbenzaldehyde (200 mg, 1.01 mmol) and indolin-2-one (134 mg, 1.01 mmol) in ethanol (10 mL) was treated with piperidine (0.099 mL, 1.01 mmol) and heated at 80-85° C. After 15.25 h, the solution was cooled to rt and concentrated. The residue was purified by column chromatography (eluting with a gradient from 80:20 to 30:70 hexane-ethyl acetate) to provide 3-(3-bromo-2-methylbenzylidene)indolin-2-one as a bright yellow solid (94.9 mg, 30%). 1H NMR (400 MHz, chloroform-d) δ 7.89 (1H, br. s.), 7.85 (1H, s), 7.64 (1H, d, J=7.9 Hz), 7.47 (1H, d, J=7.7 Hz), 7.20 (1H, td, J=7.7, 1.1 Hz), 7.07-7.16 (2H, m), 6.87 (1H, d, J=7.9 Hz), 6.81 (1H, td, J=7.6, 1.0 Hz), 2.43 (3H, s). Mass spectrum m/z 314, 316 (M+H)+.

Workup

temperaturethe solution was cooled to rt
concentrationconcentrated
customThe residue was purified by column chromatography (
washeluting with a gradient from 80:20 to 30:70 hexane-ethyl acetate)

Sources & evidence

ORD record: ord-bd36c38747554e13affb5df0f8121475
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084620B2

Reaction notes

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