Ammonium formate → HCID 59300541、化合物

HRID 603401ノート

反応式

HRID 603401 の反応式
[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

参加物

5

反応物 2

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

生成物 1

HCID 59300541HCID 59300541、化合物収率 88.1%

試薬・触媒・溶媒 2

HCID 9942167Palladium hydroxide触媒HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-40e776cf87684da8a48048bc6c3112b6
出典データセット
uspto-grants-2011_03
特許番号
US07906653B2

反応ノート

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