4-Fluoro-3-(trifluoromethyl)aniline → 6-(Pyrimidin-4-yloxy)-benzo[d]isoxazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

HRID 556349Notes

Reaction equation

HRID 556349 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[C:9]([F:12])([F:11])[F:10].C[Al](C)C.C([O:19][C:20]([C:22]1[C:26]2[CH:27]=[CH:28][C:29]([O:31][C:32]3[CH:37]=[CH:36][N:35]=[CH:34][N:33]=3)=[CH:30][C:25]=2[O:24][N:23]=1)=O)C>C1(C)C=CC=CC=1.C1COCC1>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:20]([C:22]2[C:26]3[CH:27]=[CH:28][C:29]([O:31][C:32]4[CH:37]=[CH:36][N:35]=[CH:34][N:33]=4)=[CH:30][C:25]=3[O:24][N:23]=2)=[O:19])=[CH:4][C:3]=1[C:9]([F:10])([F:11])[F:12]

Participants

6

Reactant 3

HCID 753774-Fluoro-3-(trifluoromethyl)anilineHCID 16682925TrimethylaluminumHCID 669929496-(Pyrimidin-4-yloxy)-benzo[d]isoxazole-3-carboxylic acid ethyl ester

Product 1

HCID 236584896-(Pyrimidin-4-yloxy)-benzo[d]isoxazole-3-carboxylic acid (4-fluoro-3-trifluoromethyl-phenyl)-amide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

In a dried vessel, 46 μl (0.35 mMol) 4-fluoro-3-trifluoromethyl-aniline are dissolved in 6 ml toluene and cooled to 10° C. Then 550 μl Me3Al (2 M in toluene; 1.1 mMol) are added via syringe. After 1 h at rt, a solution of 101 mg (0.35 mMol) 6-(pyrimidin-4-yloxy)-benzo[d]isoxazole-3-carboxylic acid ethyl ester in 1.25 ml THF is added and the reaction mixture stirred for 25 min in an oil bath at 110° C. Work up as described in step 1.2 gives the title compound: MS: [M−1]=419; Anal.: C,H,N,F.

Sources & evidence

ORD record
ord-480ce5baa9a04251a59910474c98d590
Source dataset
uspto-grants-2011_11
Patent number
US08058276B2

Reaction notes

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