Sodium hydride → HCID 16730928, compound

HRID 226951Notes

Reaction equation

HRID 226951 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[C:8]([C:10]([C:12]2[C:21](=[O:22])[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[NH:14][CH:13]=2)=[O:11])[CH:7]=[CH:6][N:5]=1.[F:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26]Br>CN(C)C=O>[F:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21](=[O:22])[C:12]([C:10]([C:8]2[CH:7]=[CH:6][N:5]=[C:4]([CH3:3])[CH:9]=2)=[O:11])=[CH:13]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 57754702HCID 57754702, compound

Product 1

HCID 16730928HCID 16730928, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4ee was prepared following the procedure outlined in Step 3 of Example 1 using 10.4 mg (0.26 mmol) of sodium hydride (60%), 53 mg (0.20 mmol) of 3-(2-methyl-pyridine-4-carbonyl)-1H-quinolin-4-one 3h, 3 mL of anhydrous dimethylformamide, and 49 mg (0.26 mmol) of 2-fluorobenzylbromide. The crude product 4ee was purified by flash chromatography to yield 21 mg of a colorless solid 4ee: LC-MSD, m/z for C23H17FN2O2, [M+H]+=373.5, [M+2H]+=374.5; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=1.296 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.60 (s, 3H), 5.43 (s, 2H), 7.02-7.20 (m, 3H), 7.32-7.40 (m, 2H), 7.40-7.47 (m, 3H), 7.64 (t, 1H), 8.44 (m, 2H), 8.60 (d, 1H).

Workup

  1. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-92a85fcd413147c5a8e3f981884ee725
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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