2-Chloro-5-iodopyridine → 1-(3-Chloro-benzyl)-3-(6-chloro-pyridine-3-carbonyl)-1H-quinolin-4-one

HRID 227082Notes

Reaction equation

HRID 227082 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]([Cl:24])[CH: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:24][C:20]1[CH:19]=[C:18]([CH:23]=[CH:22][CH:21]=1)[CH2:17][N:8]1[C:9]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:4](=[O:5])[C:6]([C:15]([C:30]2[CH:29]=[N:28][C:27]([Cl:26])=[CH:32][CH:31]=2)=[O:16])=[CH:7]1

Participants

5

Reactant 3

HCID 43971762-Chloro-5-iodopyridineHCID 577546151-(3-Chloro-benzyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amideHCID 178418918HCID 178418918, compound

Product 1

HCID 577546041-(3-Chloro-benzyl)-3-(6-chloro-pyridine-3-carbonyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60, from 600 mg (1.68 mmol) of 1-(3-chloro-benzyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 4 mL THF and 887 mg (3.70 mmol) of 2-chloro-5-iodo-pyridine in 4 mL THF with 1.93 mL 2M isopropylmagnesium chloride. Yield: 418 mg of a white powder. LC-MSD, m/z for C22H14Cl2N2O2 [M+H]+=409.0, 411.0; HPLC retention time: 3.3 min.

Sources & evidence

ORD record
ord-aed9548572ca472ca6b60dad86b221e3
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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