Tetrahydrofuran → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(5,6-dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one

HRID 227027Notes

Reaction equation

HRID 227027 reaction equation
CON(C)C([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[N:19]=2)[CH:7]=1)=O.I[C:27]1[CH:28]=[C:29]([CH3:34])[C:30]([CH3:33])=[N:31][CH:32]=1.C([Mg]Cl)(C)C.C1C[O:43][CH2:42]C1>>[Br:24][C:20]1[N:19]=[C:18]([CH2:17][N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:15](=[O:16])[C:6]([C:42]([C:27]3[CH:32]=[N:31][C:30]([CH3:33])=[C:29]([CH3:34])[CH:28]=3)=[O:43])=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 206625845-Iodo-2,3-dimethylpyridineHCID 577545321-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amideHCID 178418918HCID 178418918, compound

Product 1

HCID 167312451-(6-Bromo-pyridin-2-ylmethyl)-3-(5,6-dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one

Procedure

Prepared from 402 mg (1.0 mmol) of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 3 mL THF and 513 mg (2.2 mmol) of 5-iodo-2,3-dimethyl-pyridine in 5 mL THF with 1.15 mL 2M isopropylmagnesium chloride. Yield: 296 mg of a white powder. LC-MSD, m/z for C23H18BrN3O2 [M+H]+=448.0, 450.0; HPLC retention time: 1.9 min.

Sources & evidence

ORD record
ord-957784e90e2a43dca78eb32a099dd910
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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