Sodium hydride → HCID 16731172, compound

HRID 226933Notes

Reaction equation

HRID 226933 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([C:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)=[O:10])=[N:6][C:7]=1[CH3:8].[H-].[Na+].[F:24][C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1[CH2:27]Br>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([C:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:27][C:26]3[CH:29]=[CH:30][CH:31]=[CH:32][C:25]=3[F:24])[CH:12]=2)=[O:10])=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 577545223-(5,6-Dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one

Product 1

HCID 16731172HCID 16731172, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4i was prepared following the procedure outlined in Step 3 of Example 1. Briefly described here, 32 mg (0.12 mmol) of 3-(5,6-dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one 3d, 6 mg (0.14 mmol) of 60% sodium hydride and 26 mg (0.14 mmol) of 2-fluorobenzyl bromide were combined in 0.5 mL N,N-dimethylformamide and stirred at rt for 2 h. The product was purified using reverse phase HPLC, mobile phase with a gradient 10-70% acetonitrile in 50 min. The HPLC fractions containing pure product were lyophilized to give 43 mg of a pale yellow solid 4i as trifluoroacetate salt: LC-MSD, m/z for C24H19FN2O2 [M+H]+=387.5, HPLC retention time: 1.8 min; 1H NMR (400 MHz, CDCl3): δ 2.5 (s, 3H), 2.8 (s, 3H), 5.7 (s, 2H), 7.1-7.2 (m, 3H), 7.3-7.4 (m, 1H), 7.5-7.6 (m, 1H), 7.6-7.7 (m, 1H), 7.7-7.8 (m, 1H), 8.1-8.2 (m, 1H), 8.5-8.6 (m, 1H), 9.05 (s, 1H).

Workup

  1. customCompound 4i was prepared
  2. customThe product was purified
  3. customin 50 min
  4. additionThe HPLC fractions containing pure product

Sources & evidence

ORD record
ord-31b19680f36d4054906c8b768f04fc57
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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