1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide → HCID 57754741, compound

HRID 227043Notes

Reaction equation

HRID 227043 reaction equation
CON(C)[C:4]([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:5].I[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][O:36][CH3:37])=[C:29]([CH3:38])[CH:28]=1.C([Mg]Cl)(C)C>C1COCC1>[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:4](=[O:5])[C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][CH2:35][O:36][CH3:37])=[C:29]([CH3:38])[CH:28]=3)=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 577545321-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amideHCID 66879118HCID 66879118, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 57754741HCID 57754741, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60 from 120 mg (0.30 mmol) of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 2 mL THF and 192 mg (0.66 mmol) of 4-iodo-1-(2-methoxy-ethoxy)-2-methyl-benzene in 2 mL THF with 0.34 mL 2M isopropylmagnesium chloride. Yield: 39 mg of a white powder. LC-MSD, m/z for C26H23BrN2O4 [M+H]+=507.0, 509.0; HPLC retention time: 2.5 min.

Sources & evidence

ORD record
ord-b2b875b812674eaca8149a422b3ec11e
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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