Dimethylamine → 6-Bromo-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

HRID 17438Notes

Reaction equation

HRID 17438 reaction equation
[Br:1][C:2]1[C:3]([F:15])=[C:4]2[O:8][C:7](Cl)=[N:6][C:5]2=[C:10]([C:13]#[N:14])[C:11]=1[CH3:12].[CH:16]([N:19](C(C)C)[CH2:20]C)(C)C.CNC>ClCCl>[Br:1][C:2]1[C:3]([F:15])=[C:4]2[O:8][C:7]([N:19]([CH3:20])[CH3:16])=[N:6][C:5]2=[C:10]([C:13]#[N:14])[C:11]=1[CH3:12]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 685849876-Bromo-2-chloro-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile

Product 1

HCID 685849786-Bromo-2-(dimethylamino)-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrileYield 56.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

6-Bromo-2-chloro-7-fluoro-5-methyl-1,3-benzoxazole-4-carbonitrile (I-167) (1.93 g, 6.67 mmol) was dissolved in dichloromethane (40 ml), then diisopropylethylamine (1.20 ml, 7.06 mmol) and dimethylamine (2.0 M tetrahydrofuran solution, 5.00 ml, 10.0 mmol) were added. After stirring with heating under reflux overnight, this was diluted with dichloromethane. After washing with water and drying over anhydrous sodium sulfate, the solvent was evaporated away under reduced pressure, then the resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=70:1) to obtain a yellow solid (1.12 g, 56%).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux overnight
  3. washAfter washing with water
  4. dry with materialdrying over anhydrous sodium sulfate
  5. customthe solvent was evaporated away under reduced pressure
  6. customthe resulting residue was purified by silica gel column chromatography (dichloromethane to dichloromethane:methanol=70:1)

Sources & evidence

ORD record
ord-a91d2085657f4028bf7bb5702d292cd4
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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