m-Xylyl bromide → HCID 16730930, compound

HRID 226953Notes

Reaction equation

HRID 226953 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.[CH3:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27]Br>CN(C)C=O>[CH3:23][C:24]1[CH:25]=[C:26]([CH:29]=[CH:30][CH:31]=1)[CH2:27][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 12099m-Xylyl bromideHCID 24758Sodium hydrideHCID 57754702HCID 57754702, compound

Product 1

HCID 16730930HCID 16730930, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4gg 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 mg (0.26 mmol) of 3-methylbenzylbromide. The crude product was purified by preparative HPLC to yield 27 mg of a colorless solid 4gg: LC-MSD, m/z for C24H20N2O2, [M+H]+=369.5, [M+2H]+=370.5; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=1.605 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.35 (s, 3H), 2.61 (s, 3H), 5.40 (s, 2H), 7.00 (d, 2H), 7.15 (d, 1H), 7.25 (t, 1H), 7.35 (d, 1H), 7.39-7.46 (m, 3H), 7.60 (t, 1H), 8.40-8.46 (m, 2H), 8.60 (d, 1H).

Workup

  1. customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-3a42155071474d8fa74021bbce018e5c
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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