Ammonium Chloride → 7-methyl-1H-pyrazolo[3,4-c]pyridine

HRID 1527295노트

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HRID 1527295 반응식
[CH3:1][Al](C)C.Cl[C:6]1[N:7]=[CH:8][CH:9]=[C:10]2[CH:14]=[N:13][NH:12][C:11]=12.[NH4+].[Cl-]>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:6]1[N:7]=[CH:8][CH:9]=[C:10]2[CH:14]=[N:13][NH:12][C:11]=12

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 126684917-Chloro-1H-pyrazolo[3,4-c]pyridineHCID 16682925Trimethylaluminum

생성물 1

HCID 682837107-methyl-1H-pyrazolo[3,4-c]pyridine

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 8028Tetrahydrofuran용매

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온도
65 °C

실험 절차

Trimethylaluminum (23.9 mL, 47.8 mmol, 2M sol. in toluene) was added to a vigorously stirred solution of 7-chloro-1H-pyrazolo[3,4-c]pyridine (3.67 g, 23.9 mmol) and Pd(PPh3)4 (1.38 g, 1.19 mmol) in THF (109 mL) under argon. The reaction mixture was stirred at 65° C. for 16 h. The mixture was cooled to RT and poured into sat. aq. NH4Cl. The resulting suspension was filtered, the solid washed with water and discarded. The filtrate and the combined washings were extracted with EtOAc (3×). The combined organic extracts were washed with brine then dried (Phase separator) and concentrated under reduced pressure to give 7-methyl-1H-pyrazolo[3,4-c]pyridine as a solid. MS (LC-MS): 134 [M+H]+, tR (HPLC conditions k): 0.25 min.

후처리

  1. temperatureThe mixture was cooled to RT
  2. filtrationThe resulting suspension was filtered
  3. washthe solid washed with water
  4. extractionThe filtrate and the combined washings were extracted with EtOAc (3×)
  5. washThe combined organic extracts were washed with brine
  6. customthen dried (Phase separator)
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-7c17cfda322e4c70972e06541d8ee815
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085555B2

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