5-Bromo-2-iodopyrimidine → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(5-bromo-pyrimidine-2-carbonyl)-1H-quinolin-4-one

HRID 227044Notes

Reaction equation

HRID 227044 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].[Br:26][C:27]1[CH:28]=[N:29][C:30](I)=[N:31][CH:32]=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]([C:30]3[N:31]=[CH:32][C:27]([Br:26])=[CH:28][N:29]=3)=[O:5])=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 70066515-Bromo-2-iodopyrimidineHCID 577545321-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amideHCID 178418918HCID 178418918, compound

Product 1

HCID 577547211-(6-Bromo-pyridin-2-ylmethyl)-3-(5-bromo-pyrimidine-2-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 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 1 mL THF and 187 mg (0.66 mmol) of 5-bromo-2-iodo-pyrimidine in 2 mL THF with 0.34 mL 2M isopropylmagnesium chloride. Yield: 31 mg of a white powder. LC-MSD, m/z for C20H12Br2N4O2 [M+H]+=498.9, 500.9, 502.9; HPLC retention time: 2.2 min.

Sources & evidence

ORD record
ord-32f2cd461f0d4579a81d0ec6591e7237
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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