3-Tert-butyl-isoxazole-5-carboxylic acid [2-methoxy-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-4-yl]-amide → HCID 178494019, compound

HRID 570217Notes

Reaction equation

HRID 570217 reaction equation
[CH3:1][O:2][C:3]1[C:8]([N+:9]([O-])=O)=[C:7]([NH:12][C:13]([C:15]2[O:19][N:18]=[C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:16]=2)=O)[CH:6]=[C:5]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]([F:33])([F:32])[F:31])[N:4]=1>CC(O)=O.[Fe]>[C:20]([C:17]1[CH:16]=[C:15]([C:13]2[NH:9][C:8]3[C:3]([O:2][CH3:1])=[N:4][C:5]([C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]([F:33])([F:32])[F:31])=[CH:6][C:7]=3[N:12]=2)[O:19][N:18]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

4

Reactant 1

HCID 674099163-Tert-butyl-isoxazole-5-carboxylic acid [2-methoxy-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-4-yl]-amide

Product 1

HCID 178494019HCID 178494019, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-tert-butyl-isoxazole-5-carboxylic acid [2-methoxy-3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-4-yl]-amide (110 mg, 0.237 mmol, prepared as described in STEP C above) in AcOH (5 mL) was treated with iron powder (66.1 mg, 1.18 mmol), and the mixture was heated to 100° C. for 3 h. The AcOH was removed in vacuo. The residue was taken up in saturated aqueous NaHCO3 (50 mL) and extracted twice with EtOAc (50 mL). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified on a 12-g SEPRA Si 50 SPE column (Flow rate=15 mL/min; Eluent=EtOAc-hexanes, 1:99 for 10 min, then 1:99 to 1:3 over 40 min). The chromatography was repeated as above to yield 2-(3-tert-butyl-isoxazol-5-yl)-4-methoxy-6-(2-trifluoromethyl-phenyl)-3H-imidazo[4,5-c]-pyridine as a white solid. Mass Spectrum (LCMS, APCI pos.): Calculated for C21H19N4O2F3: 417.1 (M+H); Measured: 417.1.

Workup

  1. customThe AcOH was removed in vacuo
  2. extractionextracted twice with EtOAc (50 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on a 12-g SEPRA Si 50 SPE column (Flow rate=15 mL/min
  6. wait1:99 to 1:3 over 40 min)

Sources & evidence

ORD record
ord-4cd293b4dc6c4ca8a96e157f2a01a505
Source dataset
uspto-grants-2015_05
Patent number
US09023846B2

Reaction notes

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