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

HRID 1506196노트

반응식

HRID 1506196 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 174Ethylene Glycol용매

실험 절차

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%).

후처리

  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))

출처 및 근거

ORD 기록
ord-1af054871d3443118faba8102ddedd65
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216999B2

반응 노트

불러오는 중…