2-Fluoro-5-(trifluoromethyl)aniline → HCID 178522155, compound

HRID 1898450Notes

Reaction equation

HRID 1898450 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:17]3[N:18]=[C:19]([CH:21]4[CH2:23][CH2:22]4)[O:20][C:16]=3[C:15]([C:24]([O:26]C)=O)=[CH:14][C:13]=2[N:28]=1.[F:29][C:30]1[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][C:31]=1[NH2:32].C[Al](C)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[NH:9][C:10]1[NH:11][C:12]2[C:17]3[N:18]=[C:19]([CH:21]4[CH2:23][CH2:22]4)[O:20][C:16]=3[C:15]([C:24]([NH:32][C:31]3[CH:33]=[C:34]([C:37]([F:38])([F:39])[F:40])[CH:35]=[CH:36][C:30]=3[F:29])=[O:26])=[CH:14][C:13]=2[N:28]=1

Participants

5

Reactant 3

HCID 1363492-Fluoro-5-(trifluoromethyl)anilineHCID 16682925TrimethylaluminumHCID 178496995HCID 178496995, compound

Product 1

HCID 178522155HCID 178522155, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 7-((2-chloro-6-fluorophenyl)amino)-2-cyclopropyl-8H-imidazo[4′,5′:5,6]-benzo[1,2-d]oxazole-4-carboxylate (Intermediate-59, 0.050 g, 0.125 mmol) in dry toluene (5.0 mL) was added 2-fluoro-5-trifluoromethylaniline (0.022 g, 0.125 mmol) and trimethyl aluminium (2M solution in toluene) (0.009 g, 0.125 mmol). The reaction mass was refluxed for 1 h. The reaction mass was quenched with water and extracted with 10% DCM: MeOH. The organic layer was dried over anhydrous sodium sulphate and concentrated. The obtained crude was purified by column chromatography to afford 0.012 g of the desired product. 1HNMR (DMSO-d6): δ 1.23 (m, 4H), 2.33 (m, 1H), 7.40-7.47 (m, 3H), 7.62 (m, 2H), 7.75 (s, 1H), 8.68 (s, 1H), 9.42 (s, 1H), 9.89 (s, 1H), 11.69 (s, 1H); MS [M+H]+: 547.81.

Workup

  1. temperatureThe reaction mass was refluxed for 1 h
  2. customThe reaction mass was quenched with water
  3. extractionextracted with 10% DCM
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customThe obtained crude
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-68ced7b6868849c2af2ff7d968dd1a93
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

Loading…