Dimethylformamide → HCID 16731011, compound

HRID 226956Notes

Reaction equation

HRID 226956 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([C:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)=[O:8].CN(C)C=O.[F:29][C:30]([F:40])([F:39])[C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33]Br>C(#N)C>[CH3:3][C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:7]([C:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:33][C:32]2[CH:35]=[CH:36][CH:37]=[CH:38][C:31]=2[C:30]([F:29])([F:39])[F:40])[CH:10]=1)=[O:8]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 577545153-(3,4-Dimethyl-benzoyl)-1H-quinolin-4-one

Product 1

HCID 16731011HCID 16731011, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Compound 4kk was prepared following the procedure outlined in Step 3 of Example 1 using 26 mg (0.65 mmol) of sodium hydride (60%), 138.6 mg (0.50 mmol) of 3-(3,4-Dimethyl-benzoyl)-2,3-dihydro-1H-quinolin-4-one 3a, 3 mL of anhydrous dimethylformamide, and 155.4 mg (0.65 mmol) of 2-trifluoromethylbenzylbromide. The crude product was purified by flash chromatography to yield 96 mg of 4kk as a colorless solid: LC-MSD, m/z for C26H20F3NO2, [M+H]+=436.5, [M+2H]+=437.5; Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.709 min; 1H NMR (400 MHz, CDCl3/HCl): δ 2.32 (d, 6H), 5.60 (s, 2H), 6.92 (m, 1H), 7.17 (t, 2H), 7.39-7.47 (m, 3H), 7.54-7.60 (m, 2H), 7.65 (s, 1H), 7.79 (m, 1H), 8.22 (s, 1H), 8.50 (m, 1H).

Workup

  1. customCompound 4kk was prepared
  2. customThe crude product was purified by flash chromatography
  3. customto yield 96 mg of 4kk as a colorless solid

Sources & evidence

ORD record
ord-7adf7b30e31f40199c7d2c729f89cc97
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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