Sodium hydride → HCID 16731007, compound

HRID 226955Notes

Reaction equation

HRID 226955 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[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])[CH:4]=1.[F:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25]Br>CN(C)C=O>[F:22][C:23]1[CH:30]=[CH:29][CH:28]=[CH:27][C:24]=1[CH2:25][N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20](=[O:21])[C:11]([C:9]([C:5]2[CH:4]=[N:3][CH:8]=[CH:7][CH:6]=2)=[O:10])=[CH:12]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 57754566HCID 57754566, compound

Product 1

HCID 16731007HCID 16731007, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4ii was prepared following the procedure outlined in Step 3 of Example 1 using 16 mg (0.40 mmol) of sodium hydride (60%), 75 mg (0.30 mmol) of 3-(pyridine-3-carbonyl)-1H-quinolin-4-one, 3 mL of anhydrous dimethylformamide, and 75.6 mg (0.4 mmol) of 2-fluorobenzylbromide. The crude product was purified by flash chromatography to yield 35 mg of a colorless solid 4ii: LC-MSD, m/z for C22H15FN2O2, [M+H]+=359.4, [M+2H]+=360.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=1.432 min; 1H NMR (400 MHz, CDCl3HCl): δ 5.46 (s, 2H), 7.02-7.20 (m, 3H), 7.32-7.38 (m, 2H), 7.40-7.46 (m, 2H), 7.64 (t, 1H), 8.08 (d, 1H), 8.45 (d, 2H), 8.71 (d, 1H), 8.98 (s, 1H).

Workup

  1. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-095e5f7ac94f4710bb9b33104f67c4fb
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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