Dimethylformamide → HCID 16731009, compound

HRID 226954Notes

Reaction equation

HRID 226954 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.CN(C)C=O.[CH3:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31]Br>C(#N)C>[CH3:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][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

6

Reactant 4

HCID 6228DimethylformamideHCID 12099m-Xylyl bromideHCID 24758Sodium hydrideHCID 57754566HCID 57754566, compound

Product 1

HCID 16731009HCID 16731009, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 4hh 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 74.0 mg (0.4 mmol) of 3-methylbenzylbromide. The crude product was purified by flash chromatography to yield 35 mg of 4hh as a colorless solid: LC-MSD, m/z for C23H18N2O2, [M+H]+=355.4, [M+2H]+=356.4; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=1.710 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.36 (s, 3H), 5.41 (s, 2H), 7.00 (d, 2H), 7.12-7.28 (m, 2H), 7.34-7.45 (m, 3H), 7.60 (m, 1H), 8.09 (m, 1H), 8.42-8.46 (m, 2H), 8.71 (m, 2H), 8.99 (s, 1H).

Workup

  1. customCompound 4hh was prepared
  2. customThe crude product was purified by flash chromatography
  3. customto yield 35 mg of 4hh as a colorless solid

Sources & evidence

ORD record
ord-b71069920b89474c98bf160cc2d2ba8b
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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