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

HRID 8490

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HRID 8490 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 24458Ferrous Chloride촉매HCID 80711,2-Dimethoxyethane용매2회

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온도
15 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f81762d9fc7e453d9a6e196d69290dfb
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087618B2

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