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

HRID 1527295ノート

反応式

HRID 1527295 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-7c17cfda322e4c70972e06541d8ee815
出典データセット
uspto-grants-2015_07
特許番号
US09085555B2

反応ノート

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