Triethylamine → 5H-Imidazo[2,1-a]isoindole-2-carbaldehyde

HRID 638864

반응식

HRID 638864 반응식
Br[C:2](=[CH:5]OC(C)C)[CH:3]=[O:4].[NH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][N:12]=1.C(N(CC)CC)C>C(#N)C.C(OCC)(=O)C>[N:10]1[C:2]([CH:3]=[O:4])=[CH:5][N:12]2[CH2:13][C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:11]=12

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 4278591H-isoindol-3-amineHCID 534166342-Bromo-3-isopropoxy-propenal

생성물 1

HCID 222245345H-Imidazo[2,1-a]isoindole-2-carbaldehyde수율 22%

시약·촉매·용매 2

HCID 6342Acetonitrile용매2회HCID 8857Ethyl Acetate용매

실험 절차

The solution of 2-bromo-3-isopropoxy-propenal (4.97 g) in dry acetonitrile (3 mL) was added to the mixture of 3-amino-1H-isoindole (3.4 g) in dry acetonitrile (100 mL). The reaction mixture was stirred for 3.25 h at room temperature. Then triethylamine (3.6 mL) was added to the mixture and heated to reflux for 2 h. The mixture was cooled to room temperature, diluted with ethyl acetate, and washed with 20% potassium hydrogen carbonate. After filtration through a pad of Celite, the organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was applied to silica gel column chromatography, then eluted with ethyl acetate-hexane (3/1˜4/1). The crude compound was crystallized from ethyl acetate and n-hexane to give the title compound (1.04 g, 22%). 1H NMR (400 MHz, CDCl3) δ 5.01 (s, 2H), 7.28-7.52 (m, 3H), 7.90 (s, 1H), 7.91-7.93 (m, 1H), 9.92 (s, 1H).

후처리

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. temperatureThe mixture was cooled to room temperature
  4. washwashed with 20% potassium hydrogen carbonate
  5. filtrationAfter filtration through a pad of Celite
  6. dry with materialthe organic layer was dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. washeluted with ethyl acetate-hexane (3/1˜4/1)
  9. customThe crude compound was crystallized from ethyl acetate and n-hexane

출처 및 근거

ORD 기록
ord-4260d991ba114747a5939e03169a3567
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691842B2

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