Pyridine → 1-(6-Bromo-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]-1-yl)ethanone

HRID 1618499ノート

反応式

HRID 1618499 の反応式
[Br:1][C:2]1[CH:7]=[C:6]2[NH:8][CH2:9][C:10]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>CN(C1C=CN=CC=1)C>[Br:1][C:2]1[CH:7]=[C:6]2[N:8]([C:22](=[O:24])[CH3:23])[CH2:9][C:10]3([CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)[C:5]2=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 582218836-Bromo-1,2-dihydrospiro(indole-3,4'-oxane)

生成物 1

HCID 672853631-(6-Bromo-2',3',5',6'-tetrahydrospiro[indoline-3,4'-pyran]-1-yl)ethanone

試薬・触媒・溶媒 1

HCID 142844-(Dimethylamino)pyridine触媒

反応条件

温度
85 °C

実験手順

6-Bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran] (2.53 g, 9.44 mmol) was dissolved in pyridine (8.39 mL, 104 mmol) and acetic anhydride (1.34 mL, 14.2 mmol) was added followed by DMAP (0.0576 g, 0.472 mmol). The reaction was heated to 85° C. for 90 min. After this time the reaction was concentrated in vacuo and the resulting oil was partitioned between EtOAc and 0.5N HCl. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by column chromatography to give 1-(6-bromo-2′,3′,5′,6′-tetrahydrospiro[indoline-3,4′-pyran]-1-yl)ethanone.

後処理

  1. concentrationAfter this time the reaction was concentrated in vacuo
  2. customthe resulting oil was partitioned between EtOAc and 0.5N HCl
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography

出典と根拠

ORDレコード
ord-3f7aee9c982f4324b68eb03befddf701
出典データセット
uspto-grants-2014_07
特許番号
US08765940B2

反応ノート

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