HCID 67411418, compound → HCID 136073160, compound

HRID 1191241Notes

Reaction equation

HRID 1191241 reaction equation
[N+:1]([C:4]1[C:5]([NH:20][C:21]([C:23]2[O:27][N:26]=[C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:24]=2)=O)=[N:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])=[CH:8][CH:9]=1)([O-])=O>C(O)(=O)C.[Fe]>[C:28]([C:25]1[CH:24]=[C:23]([C:21]2[NH:1][C:4]3[C:5]([N:20]=2)=[N:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])=[CH:8][CH:9]=3)[O:27][N:26]=1)([CH3:31])([CH3:30])[CH3:29]

Participants

4

Reactant 1

HCID 67411418HCID 67411418, compound

Product 1

HCID 136073160HCID 136073160, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 3-tert-butyl-isoxazole-5-carboxylic acid [3-nitro-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide (78.0 mg, 0.180 mmol, prepared as described in the previous step) in acetic acid (5 mL) was treated with iron powder (50.1 mg, 0.898 mmol) and heated to 100° C. for 2 h. The volume of acetic acid was reduced to 2 mL by concentrating in vacuo, and saturated aqueous NaHCO3 (50 mL) was added. The resulting mixture was extracted twice with EtOAc (60 mL). The combined extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified on a 4-g SEPRA Si 50 SPE column (Isco system: Flow rate=10 mL/min; Eluent=EtOAc/hexanes, 1:99 v/v for 5 min, then 1:99 to 1:9 v/v over 40 min) to yield 2-(3-tert-butyl-isoxazol-5-yl)-5-(2-trifluoromethyl-phenyl)-1H-imidazo[4,5-b]pyridine as a white solid. 1H-NMR (400 MHz, CDCl3) δ: 10.06 (br. s., 1H), 8.16 (d, J=8.3 Hz, 1H), 7.81 (d, J 8.1 Hz, 1H), 7.64 (d, J=7.6 Hz, 1H), 7.52-7.60 (m, 2H), 7.46 (d, J=8.3 Hz, 1H), 7.07 (s, 1H), 1.42 (s, 9H). Mass Spectrum (LCMS, APCI pos.): Calculated for C20H17F3N4O: 387.1 (M+H); Measured: 387.1.

Workup

  1. concentrationby concentrating in vacuo, and saturated aqueous NaHCO3 (50 mL)
  2. additionwas added
  3. extractionThe resulting mixture was extracted twice with EtOAc (60 mL)
  4. dry with materialThe combined extracts were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on a 4-g SEPRA Si 50 SPE column (Isco system

Sources & evidence

ORD record
ord-998b32b538df422b90589b9bf4c55de5
Source dataset
uspto-grants-2014_03
Patent number
US08680098B2

Reaction notes

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