Sodium hydride → HCID 16730852, compound

HRID 226944Notes

Reaction equation

HRID 226944 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][C:27]=1[CH3:28])[C:7]([C:9]1[C:18](=[O:19])[C:17]2[CH:16]=[C:15]3[O:20][C:21]([F:24])([F:23])[O:22][C:14]3=[CH:13][C:12]=2[NH:11][CH:10]=1)=[O:8].[F:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32]Br>CN(C)C=O>[CH3:3][C:4]1[CH:5]=[C:6]([CH:25]=[CH:26][C:27]=1[CH3:28])[C:7]([C:9]1[C:18](=[O:19])[C:17]2[CH:16]=[C:15]3[O:20][C:21]([F:23])([F:24])[O:22][C:14]3=[CH:13][C:12]=2[N:11]([CH2:32][C:31]2[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=2[F:29])[CH:10]=1)=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 67968alpha-Bromo-o-fluorotolueneHCID 57754581HCID 57754581, compound

Product 1

HCID 16730852HCID 16730852, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 4v was prepared following the procedure outlined in Step 3 of Example 1 using 10.4 mg (0.26 mmol) of sodium hydride (60%), 71 mg (0.20 mmol) of 7-(3,4-dimethyl-benzoyl)-2,2-difluoro-5H-[1,3]dioxolo[4,5-g]quinolin-8-one, 3 mL of anhydrous dimethylformamide, and 49.1 mg (0.26 mmol) of 2-fluorobenzylbromide. The crude product was purified by flash chromatography to yield 29 mg of 4v as a colorless solid: Reverse phase HPLC (gradient acetonitrile 0.1% TFA 20-95% in 4 min) retention time=2.922 min; LC-MSD, m/z for C24H18F3NO4, [M+H]+=466.4, [M+2H]+=467.4; 1H NMR (400 MHz, CDCl3/HCl): δ 2.2-2.4 (d, 6H), 5.40 (s, 2H), 7.02-7.10 (m, 2H), 7.12-7.22 (m, 3H), 7.34-7.42 (m, 1H), 7.52-7.57 (d, 1H), 7.62 (s, 1H), 8.10 (s, 1H), 8.24 (s, 1H).

Workup

  1. customCompound 4v was prepared
  2. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-e1cafa6d954848ebbda13aefb6e9850d
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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