2-Chloro-5-iodopyridine → HCID 57754623, compound

HRID 227078Notes

Reaction equation

HRID 227078 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]([CH3:24])[N:19]=2)[CH:7]=1)=[O:5].[Cl:26][C:27]1[CH:32]=[CH:31][C:30](I)=[CH:29][N:28]=1.C([Mg]Cl)(C)C>C1COCC1>[Cl:26][C:27]1[N:28]=[CH:29][C:30]([C:4]([C:6]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=3)[CH:7]=2)=[O:5])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 43971762-Chloro-5-iodopyridineHCID 577545121-(6-Methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl amideHCID 178418918HCID 178418918, compound

Product 1

HCID 57754623HCID 57754623, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60, from 800 mg (2.37 mmol) of 1-(6-methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 25 mL THF and 1.25 g (5.22 mmol) of 2-chloro-5-iodo-pyridine in 7 mL THF with 2.73 mL 2M isopropylmagnesium chloride. Yield: 635 mg of a white powder. LC-MSD, m/z for C22H16ClN3O2 [M+H]+=390.1, 392.0; HPLC retention time: 2.0 min.

Sources & evidence

ORD record
ord-b88a176329ee41d59bf5c690c5774826
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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