Triethylamine → 7-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine

HRID 8490

反応式

HRID 8490 の反応式
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[N:10]O)[CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C>COCCOC.[Fe](Cl)Cl>[Cl:1][C:2]1[N:7]2[N:10]=[C:9]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:8]=[C:6]2[CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 728244482-(6-Chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone oxime

生成物 1

HCID 111841947-Chloro-2-(4-fluorophenyl)pyrazolo[1,5-a]pyridine収率 68.3%

試薬・触媒・溶媒 2

HCID 24458Ferrous Chloride触媒HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
15 °C

実験手順

To a solution of 2-(6-chloro-2-pyridinyl)-1-(4-fluorophenyl)ethanone oxime (109.2 g, 414 mmol) in 1,2-dimethoxyethane (500 mL) at 0° C. was added trifluoroacetic anhydride (59 mL, 414 mmol), keeping the temperature below 10° C. After the addition was complete, the reaction was warmed to 15° C. The solution was then cooled to 4° C. and a solution of triethylamine (116 mL, 828 mmol) in 1,2-dimethoxyethane (60 mL) was added over 0.5 hours. After warming to room temperature, the mixture was stirred for 1.5 hours. To this was added iron(II) chloride (0.52 g, 4.1 mmol) and the reaction was heated to reflux for 3 hours. The reaction was concentrated and the resulting solid was recrystallized from ethyl acetate-hexanes to give 7-chloro-2-(4-fluorophenyl)pyrazolo[1.5-α]pyridine (69.7 g. 68%) as off-white needles. 1H NMR (CDCl3): δ 8.03 (m, 2 H), 7.54 (d, 1 H), 7.16 (m, 3 H), 6.93 (d, 1 H), 6.91 (s, 1 H); MS m/z 247 (M+1); mp 156–157° C.

後処理

  1. customthe temperature below 10° C
  2. additionAfter the addition
  3. temperatureThe solution was then cooled to 4° C.
  4. temperatureAfter warming to room temperature
  5. temperaturethe reaction was heated
  6. temperatureto reflux for 3 hours
  7. concentrationThe reaction was concentrated
  8. customthe resulting solid was recrystallized from ethyl acetate-hexanes

出典と根拠

ORDレコード
ord-f81762d9fc7e453d9a6e196d69290dfb
出典データセット
uspto-grants-2006_08
特許番号
US07087618B2

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