Hydrochloric Acid → HCID 178481757、化合物

HRID 2204661ノート

反応式

HRID 2204661 の反応式
Cl[C:2]1[C:7]([CH:8]=O)=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12.[CH3:13][NH:14][NH2:15].Cl.O>CCCCO>[CH3:13][N:14]1[C:2]2=[C:3]3[CH:12]=[CH:11][NH:10][C:4]3=[N:5][CH:6]=[C:7]2[CH:8]=[N:15]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 6061MethylhydrazineHCID 242292744-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

生成物 1

HCID 178481757HCID 178481757、化合物収率 74%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

反応条件

温度
120 °C

実験手順

4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1.37 g, 7.59 mmol, Adesis) and methylhydrazine (0.599 mL, 11.4 mmol) in n-BuOH (7 mL) were heated to about 95° C. After about 15 min, concentrated HCl (0.500 mL, 16.4 mmol) was added and the reaction mixture was heated to about 120° C. After about 4 h, water (10 mL) was added and the mixture was extracted with EtOAc (20 mL). The organic layer was separated and the aqueous layer was basified with saturated aqueous NaHCO3 to about pH 8 and extracted with EtOAc (2×20 mL). The combined organic layers were dried over anhydrous MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (40 g column) eluting with a gradient of 5-60% EtOAc in heptane to give 1-methyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridine (0.960 g, 74%): LC/MS (Table 2, Method d) Rt=1.40 min; MS m/z: 173 (M+H)+.

後処理

  1. waitAfter about 4 h
  2. extractionthe mixture was extracted with EtOAc (20 mL)
  3. customThe organic layer was separated
  4. extractionextracted with EtOAc (2×20 mL)
  5. dry with materialThe combined organic layers were dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel chromatography (40 g column)
  9. washeluting with a gradient of 5-60% EtOAc in heptane

出典と根拠

ORDレコード
ord-f2fa7acef84143e193428067b0d74ec8
出典データセット
uspto-grants-2016_06
特許番号
US09365579B2

反応ノート

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