Sodium bis(trimethylsilyl)amide → Benzo[d]isoxazol-3-yl-{4-[3,5-bis(trifluoromethyl)pyrazol-1-yl]phenyl}amine

HRID 1634085Notes

Reaction equation

HRID 1634085 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17]([F:20])([F:19])[F:18])=[N:9]2)=[CH:4][CH:3]=1.Cl[C:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[O:24][N:23]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>O1CCCC1.O>[O:24]1[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=2[C:22]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([N:8]3[C:12]([C:13]([F:14])([F:15])[F:16])=[CH:11][C:10]([C:17]([F:20])([F:19])[F:18])=[N:9]3)=[CH:6][CH:7]=2)=[N:23]1

Participants

6

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 27406684-(3,5-Bis(trifluoromethyl)-1H-pyrazol-1-yl)anilineHCID 27797803-Chloro-1,2-benzoxazole

Product 1

HCID 18677108Benzo[d]isoxazol-3-yl-{4-[3,5-bis(trifluoromethyl)pyrazol-1-yl]phenyl}amineYield 18.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 1-(4′-aminophenyl)-3,5-bis(trifluoromethyl)pyrazole (0.20 g, 0.68 mmol) and 3-chlorobenzisoxazole (0.10 g, 0.65 mmol) in tetrahydrofuran (2.5 mL) under argon was added sodium bis-trimethylsilyl amide (1.0 M in tetrahydrofuran, 0.68 mL, 0.68 mmol). After seven days, the mixture was diluted with water, and extracted with ethyl acetate. The organic layer was washed with brine, dried (magnesium sulfate) and concentrated. The residue was purified by flash chromatography (elution with ethyl acetate/hexanes) to give the above-named compound (0.050 g). m.p. 209-210° C. NMR (CDCl3, 400 MHz): δ 7.77 (d, 1H), 7.64 (m, 3H), 7.53 (d, 2H), 7.37 (m, 1H), 7.09 (s, 1H), 6.68 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (elution with ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-cc25dd9428d44dbcaa12b3571a28b867
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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