Sodium hydride → 2-((1H-indol-3-yl)methyl)-9-(benzo[d]oxazol-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41557ノート

反応式

HRID 41557 の反応式
[H-].[Na+].[O:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[N:5]=[C:4]1[N:12]1[CH2:23][CH2:22][C:15]2([C:20](=[O:21])[NH:19][CH2:18][CH2:17][CH2:16]2)[CH2:14][CH2:13]1.Cl[CH2:25][C:26]1[C:34]2[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=2)[N:28](S(C2C=CC(C)=CC=2)(=O)=O)[CH:27]=1.[NH4+].[Cl-]>C1COCC1>[NH:28]1[C:29]2[C:34](=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:26]([CH2:25][N:19]2[CH2:18][CH2:17][CH2:16][C:15]3([CH2:22][CH2:23][N:12]([C:4]4[O:3][C:7]5[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=5[N:5]=4)[CH2:13][CH2:14]3)[C:20]2=[O:21])=[CH:27]1

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 668519953-(chloromethyl)-1-tosyl-1H-indoleHCID 672537129-(Benzo[d]oxazol-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

生成物 1

HCID 532594682-((1H-indol-3-yl)methyl)-9-(benzo[d]oxazol-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

NaH (28 mg, 1.16 mmol) was added to a stirred solution of 9-(benzo[d]oxazol-2-yl)-2,9-diazaspiro[5.5]undecan-1-one (150 mg, 0.53 mmol) in THF (5 mL) and the resulting mixture was heated under reflux for 30 min. The reaction mixture was allowed to warm to rt. Then, 3-(chloromethyl)-1-tosyl-1H-indole [471294-27-6] (201 mg, 0.63 mmol) was added and the mixture was heated at 60° C. for 18 h. The mixture was cooled to rt and saturated aqueous NH4Cl solution was added and the solution was extracted with ethyl acetate. The organic layer was washed with water and brine, filtered and dried over anhydrous sodium sulfate. The organic layer was concentrated under reduced pressure to yield a pale brown solid. This product was directly taken for the next step for detosylation to furnish the title compound as follows:

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 30 min
  3. temperaturethe mixture was heated at 60° C. for 18 h
  4. temperatureThe mixture was cooled to rt
  5. extractionthe solution was extracted with ethyl acetate
  6. washThe organic layer was washed with water and brine
  7. filtrationfiltered
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationThe organic layer was concentrated under reduced pressure
  10. customto yield a pale brown solid

出典と根拠

ORDレコード
ord-d077ed05ae284637b56eda4e62a8a4be
出典データセット
uspto-grants-2013_09
特許番号
US08530648B2

反応ノート

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