Water → 4-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

HRID 1506196ノート

反応式

HRID 1506196 の反応式
Cl[C:2]1[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12.[CH:13]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.O>C(O)CO>[CH:13]1([NH:19][C:2]2[C:7]([CH:8]=[O:9])=[CH:6][N:5]=[C:4]3[NH:10][CH:11]=[CH:12][C:3]=23)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

参加物

5

反応物 3

HCID 962WaterHCID 7965CyclohexylamineHCID 242292744-chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde

生成物 1

HCID 867266334-(Cyclohexylamino)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde収率 71%

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

実験手順

4-Chloro-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (845 mg, 4.68 mmol) and cyclohexylamine (2.5 mL, 22 mmol) in ethylene glycol (2 mL) were stirred at 170° C. for 1 hour under microwave irradiation. The reaction mixture was allowed to cool to room temperature and, after addition of water, extracted with chloroform. The organic layer was stirred with 2 M hydrochloric acid (20 mL) for 1 hour, and the organic layer was separated. The aqueous layer was adjusted to pH 9 or above with 10 M aqueous sodium hydroxide and extracted with chloroform. The organic layers were combined, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=10/1 (v/v)) to give the title compound as a pale yellow oil (804 mg, yield 71%).

後処理

  1. extractionextracted with chloroform
  2. customthe organic layer was separated
  3. extractionextracted with chloroform
  4. washwashed with saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform/methanol=10/1 (v/v))

出典と根拠

ORDレコード
ord-1af054871d3443118faba8102ddedd65
出典データセット
uspto-grants-2015_12
特許番号
US09216999B2

反応ノート

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