Ammonium formate → HCID 59300541, 화합물

HRID 2235872노트

반응식

HRID 2235872 반응식
[CH2:1]([C:4]1[C:12]([O:13]CC2C=CC=CC=2)=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[CH3:21])[CH:2]=[CH2:3].C([O-])=O.[NH4+]>CCO.[OH-].[Pd+2].[OH-]>[CH3:21][N:8]1[C:9]2[C:5](=[C:4]([CH2:1][CH2:2][CH3:3])[C:12]([OH:13])=[CH:11][CH:10]=2)[CH:6]=[CH:7]1

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 593004174-allyl-5-(benzyloxy)-1-methyl-1H-indole

생성물 1

HCID 59300541HCID 59300541, 화합물수율 88.1%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

실험 절차

4-Allyl-5-(benzyloxy)-1-methyl-1H-indole (250.0 mg, 0.90 mmol) (Example 59) was dissolved in EtOH (15 mL), then 20% palladium (II) hydroxide on carbon (30 mg) was added, followed by ammonium formate (455 mg, 7.21 mmol). After stirring for 1 h at rt, the mixture was heated to 40° C. for 2.5 h. After cooling to rt, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. Water was added to the residue, and the aqueous phase was extracted with EtOAc (2×). The combined organic phases were dried over Na2SO4, filtered, and concentrated under reduced pressure to give 150 mg (88%) of the title compound as an oil. 1H NMR (400 MHz, CDCl3): δ 1.02 (t, 3H), 1.73 (m, 2H), 2.85 (t, 2H), 3.76 (s, 3H), 4.33 (br, 1H), 6.40 (s, 1H), 6.78 (d, 1H), 7.02 (m, 2H).

후처리

  1. temperaturethe mixture was heated to 40° C. for 2.5 h
  2. temperatureAfter cooling to rt
  3. customthe catalyst was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionWater was added to the residue
  6. extractionthe aqueous phase was extracted with EtOAc (2×)
  7. dry with materialThe combined organic phases were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-b9675fbd8b5a42d4a25ffd9cd75d5fdf
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07714004B2

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