Sodium hydride → HCID 16730929, compound

HRID 226952Notes

Reaction equation

HRID 226952 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.Br[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=1>CN(C)C=O>[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)[N:14]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([CH3:31])[N:26]=3)[CH:13]=2)=[O:11])[CH:7]=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 125437332-(Bromomethyl)-6-methylpyridineHCID 57754702HCID 57754702, compound

Product 1

HCID 16730929HCID 16730929, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4ff 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 48.7 mg (0.26 mmol) of 2-bromomethyl-6-methyl-pyridine. The crude product was purified by preparative HPLC to yield 15 mg of colorless solid 4ff: LC-MSD, m/z for C23H19N3O2, [M+H]+=370.5, [M+2H]+=371.5; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=1.976 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.57 (s, 3H), 2.61 (s, 3H), 5.43 (s, 2H), 6.87 (d, 1H), 7.10 (d, 1H), 7.32-7.48 (m, 4H), 7.53 (t, 1H), 7.59 (t, 1H), 8.41 (d, 1H), 8.49 (d, 1H), 8.59 (d, 1H).

Workup

  1. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-74fdb38f070048db8a6576d2722f8e80
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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