Acetic Acid → 5-bromo-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde

HRID 1523955노트

반응식

HRID 1523955 반응식
C1N2CN3CN(C2)CN1C3.[Br:11][C:12]1[CH:13]=[C:14]2[CH:20]=[CH:19][NH:18][C:15]2=[N:16][CH:17]=1.C[C:22](O)=[O:23]>O>[Br:11][C:12]1[CH:13]=[C:14]2[C:20]([CH:22]=[O:23])=[CH:19][NH:18][C:15]2=[N:16][CH:17]=1

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 4101HexamethylenetetramineHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 247296055-bromo-1H-pyrrolo(2,3-b)pyridine-3-carbaldehyde수율 33%

시약·촉매·용매 1

HCID 962Water용매

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온도
100 °C

실험 절차

Hexamethylenetetramine (1.08 g, 7.61 mmol) was added to a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (1 g, 5 mol) in HOAc (6.34 mL). The mixture was heated at 100° Celsius for 6 hours. The reaction mixture was then cooled to rt and diluted with water. The mixture was extracted with EtOAc, dried (Na2SO4), filtered and concentrated to dryness. The residue was purified by FCC to provide the title compound (379 mg, 33%). 1H NMR (500 MHz, CDCl3) δ 10.02 (s, 1H), 8.77 (d, J=2.2, 1H), 8.48 (d, J=2.2, 1H), 7.99 (d, J=2.7, 1H).

후처리

  1. temperatureThe reaction mixture was then cooled to rt
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by FCC

출처 및 근거

ORD 기록
ord-b7f931ab8a0a43aa96bc10d808ae11ec
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09079866B2

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