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Methanol → 3-(4-Fluoro-phenyl)-5-[2-(2-fluoro-phenyl)-2H-pyrazol-3-yl]-benzo[c]isoxazole

HRID 59817
Notes
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Reaction equation

HRID 59817 reaction equation
[OH-].[Na+].CO.[F:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[C:16]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=O)=[CH:19][CH:18]=2)=[CH:15][CH:14]=[N:13]1.[F:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33]C#N)=[CH:29][CH:28]=1>O>[F:26][C:27]1[CH:32]=[CH:31][C:30]([C:33]2[O:25][N:23]=[C:20]3[CH:21]=[CH:22][C:17]([C:16]4[N:12]([C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=5[F:5])[N:13]=[CH:14][CH:15]=4)=[CH:18][C:19]=23)=[CH:29][CH:28]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 68016Benzeneacetonitrile, 4-fluoro-HCID 900327651-(2-fluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole2×

Product 1

HCID 730526873-(4-Fluoro-phenyl)-5-[2-(2-fluoro-phenyl)-2H-pyrazol-3-yl]-benzo[c]isoxazoleYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of sodium hydroxide (282 mg, 7.06 mmol) and MeOH (2.5 ml) was allowed to stir for 1 h at room temperature, 1-(2-fluoro-phenyl)-5-(4-nitro-phenyl)-1H-pyrazole (intermediate B) (200 mg, 706 μmol) and commercially available 2-(4-fluoro-phenyl)-acetonitrile (143 mg, 127 μl, 1.06 mmol) were added, and the reaction mixture was allowed to stir for 2 h at 60° C. The reaction mixture was poured into water (20 ml) and extracted with diethyl ether (2×40 ml). The combined organic layers were washed with brine (30 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (toluene/ethyl acetate 95:5) followed by crystallization (ethyl acetate/heptane) to yield the title compound as a light yellow solid (184 mg, 70%), MS (ISP) m/z=374.1 [(M+H)+], mp 171° C.

Workup

  1. stirringto stir for 2 h at 60° C
  2. extractionextracted with diethyl ether (2×40 ml)
  3. washThe combined organic layers were washed with brine (30 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude product was further purified by column chromatography on silica gel (toluene/ethyl acetate 95:5)
  7. customfollowed by crystallization (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-3cfc676d05e341a0b69c0db6b4916fd7
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09440962B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes