1,10-Phenanthroline → 1-{3-[1-(3-Nitropyridin-2-yl)piperidin-4-ylidene]prop-1-ynyl}pyrrolidin-2-one

HRID 1896021Notes

Reaction equation

Br[C:2]#[C:3][CH:4]=[C:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][CH:14]=[CH:13][N:12]=2)[CH2:7][CH2:6]1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C([O-])([O-])=O.[K+].[K+].[NH:40]1[CH2:44][CH2:43][CH2:42][C:41]1=[O:45]>CCOC(C)=O.C1(C)C=CC=CC=1>[N+:17]([C:16]1[C:11]([N:8]2[CH2:9][CH2:10][C:5](=[CH:4][C:3]#[C:2][N:40]3[CH2:44][CH2:43][CH2:42][C:41]3=[O:45])[CH2:6][CH2:7]2)=[N:12][CH:13]=[CH:14][CH:15]=1)([O-:19])=[O:18]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of Compound 261a (111 mg, 0.345 mmol), cupric sulphate (11 mg, 0.69 mmol), 1,10-phenantroline (24.9 mg, 0.138 mmol), K2CO3 (95.4 mg, 0.69 mmol), 2-pyrrolidone (39.7 μl, 0.518 mmol) and 5 mL of toluene was stirred at 80° C. for 12 h. The reaction mixture was cooled to r.t., diluted with EtOAc, washed with water, dried over Na2SO4 and evaporated to dryness in vacuo. The crude residue was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with PE-EtOAc gradient from 98:2 to 0:10, giving the title product (2 mg)

Workup

temperatureThe reaction mixture was cooled to r.t.
washwashed with water
dry with materialdried over Na2SO4
customevaporated to dryness in vacuo
customThe crude residue was purified by automated flash liquid chromatography (Horizon™-Biotage)
washeluting with PE-EtOAc gradient from 98:2 to 0:10

Sources & evidence

ORD record: ord-bde8a51850e041a696718e8f14823a94
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08518916B2

Reaction notes

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