3-(Trifluoromethyl)aniline → HCID 24762957, compound

HRID 556382Notes

Reaction equation

HRID 556382 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6].C[Al](C)C.C[O:17][C:18]([C:20]1[C:24]2[CH:25]=[CH:26][C:27]([O:29][C:30]3[CH:35]=[C:34]([CH2:36][O:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)[N:33]=[CH:32][N:31]=3)=[CH:28][C:23]=2[O:22][CH:21]=1)=O.[NH4+].[Cl-]>C1(C)C=CC=CC=1.C1COCC1.CCOC(C)=O.O>[F:1][C:2]([F:10])([F:11])[C:3]1[CH:4]=[C:5]([NH:6][C:18]([C:20]2[C:24]3[CH:25]=[CH:26][C:27]([O:29][C:30]4[CH:35]=[C:34]([CH2:36][O:37][CH2:38][C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[N:33]=[CH:32][N:31]=4)=[CH:28][C:23]=3[O:22][CH:21]=2)=[O:17])[CH:7]=[CH:8][CH:9]=1

Participants

9

Reactant 4

HCID 73753-(Trifluoromethyl)anilineHCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 575564436-(6-Benzyloxymethyl-pyrimidin-4-yloxy)-benzofuran-3-carboxylic acid methyl ester

Product 1

HCID 24762957HCID 24762957, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

In a dried vessel, 55 μl (0.44 mMol) 3-trifluoromethyl-aniline are dissolved in 6 ml toluene and cooled in an ice bath. Then 0.66 ml Me3Al (2 M in toluene; 1.32 mMol) are added via syringe. After 1 h at rt, a solution of 156 mg (0.40 mMol) 6-(6-benzyloxymethyl-pyrimidin-4-yloxy)-benzofuran-3-carboxylic acid methyl ester in 2 ml THF is added and the yellowish solution is stirred for 1¼ h in an oil bath of 110° C. The solution is cooled in an icebath and hydrolyzed with 15 ml of a sat. NH4Cl solution. After 15 min stirring, the mixture is diluted with EtOAc and water, the aq. phase separated off and extracted twice with EtOAc. The organic layers are washed with water and brine, dried (Na2SO4) and concentrated. Chromatography (Combi Flash; hexane/EtOAc 4:1→EtOAc) gives the title compound: MS: [M+1]+=520; TLC(hexane/EtOAc 2:1): Rf=0.17.

Workup

  1. temperaturecooled in an ice bath
  2. stirringAfter 15 min stirring
  3. customthe aq. phase separated off
  4. extractionextracted twice with EtOAc
  5. washThe organic layers are washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e217f802ad044c0c93f031749a048420
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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