3-Tert-butyl-isoxazole-5-carboxylic acid [3-nitro-4-trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide → 2-(3-tert-butyl-isoxazol-5-yl)-7-trifluoromethyl-5-(2-trifluoromethyl-phenyl)-1H-imidazo[4,5-b]pyridine

HRID 1481545ノート

反応式

HRID 1481545 の反応式
[N+:1]([C:4]1[C:5]([NH:24][C:25]([C:27]2[O:31][N:30]=[C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:28]=2)=O)=[N:6][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:23])([F:22])[F:21])=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])([O-])=O>CC(O)=O.[Fe]>[C:32]([C:29]1[CH:28]=[C:27]([C:25]2[NH:1][C:4]3[C:5]([N:24]=2)=[N:6][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]([F:21])([F:23])[F:22])=[CH:8][C:9]=3[C:10]([F:13])([F:12])[F:11])[O:31][N:30]=1)([CH3:33])([CH3:35])[CH3:34]

参加物

4

反応物 1

HCID 866574113-Tert-butyl-isoxazole-5-carboxylic acid [3-nitro-4-trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide

生成物 1

HCID 1360731612-(3-tert-butyl-isoxazol-5-yl)-7-trifluoromethyl-5-(2-trifluoromethyl-phenyl)-1H-imidazo[4,5-b]pyridine

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 176Acetic Acid溶媒

反応条件

温度
100 °C

実験手順

A solution of 3-tert-butyl-isoxazole-5-carboxylic acid [3-nitro-4-trifluoromethyl-6-(2-trifluoromethyl-phenyl)-pyridin-2-yl]-amide (14.6 mg, 0.029 mmol, prepared as described in STEP E above) in AcOH (3 mL) was treated with iron powder (8.12 mg, 0.145 mmol), and the resulting mixture was stirred at 100° C. for 2 h and concentrated in vacuo. The residue was taken up in saturated aqueous NaHCO3 (30 mL) and extracted twice with EtOAc (25 mL). The combined organic extracts were dried over MgSO4 and concentrated in vacuo. The residue was purified on a 4-g SEPRA Si 50 SPE column (Flow rate=10 mL/min; Eluent=EtOAc-hexanes, 1:99 for 10 min, then 1:99 to 1:4 over 40 min) to yield 2-(3-tert-butyl-isoxazol-5-yl)-7-trifluoromethyl-5-(2-trifluoromethyl-phenyl)-1H-imidazo[4,5-b]pyridine as a white solid. 1H-NMR (400 MHz, CD3OD) δ: 7.77 (d, J=7.6 Hz, 1H), 7.63-7.69 (m, 1H), 7.58-7.62 (m, 2H), 7.52-7.58 (m, 1H), 7.26 (s, 1H), 1.33 (s, 9H). Mass Spectrum (LCMS, APCI pos.): Calculated for C21H16N4OF6: 455.1 (M+H). Measured: 455.1.

後処理

  1. concentrationconcentrated in vacuo
  2. extractionextracted twice with EtOAc (25 mL)
  3. dry with materialThe combined organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified on a 4-g SEPRA Si 50 SPE column (Flow rate=10 mL/min
  6. waitEluent=EtOAc-hexanes, 1:99 for 10 min

出典と根拠

ORDレコード
ord-cf051c3aec1042d9ac5a92bf1c677bdc
出典データセット
uspto-grants-2016_08
特許番号
US09409915B2

反応ノート

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