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Potassium Carbonate → 3-(5-(tert-Butyldimethylsilyloxy)-5,6,7,8-tetrahydroquinolin-2-yl)-2-oxoindoline-5-carbonitrile

HRID 1777187
ノート
印刷プレビュー

反応式

HRID 1777187 の反応式
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]#[N:12])[CH:8]=2)[NH:3]1.[Si:13]([O:20][CH:21]1[CH2:30][CH2:29][CH2:28][C:27]2[N:26]=[C:25](Cl)[CH:24]=[CH:23][C:22]1=2)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C([O-])([O-])=O.[K+].[K+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Si:13]([O:20][CH:21]1[CH2:30][CH2:29][CH2:28][C:27]2[N:26]=[C:25]([CH:10]3[C:9]4[C:4](=[CH:5][CH:6]=[C:7]([C:11]#[N:12])[CH:8]=4)[NH:3][C:2]3=[O:1])[CH:24]=[CH:23][C:22]1=2)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrileHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 86663635HCID 86663635、化合物

生成物 1

HCID 668235213-(5-(tert-Butyldimethylsilyloxy)-5,6,7,8-tetrahydroquinolin-2-yl)-2-oxoindoline-5-carbonitrile収率 40%

試薬・触媒・溶媒

2
HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

To a suspension of 2-oxoindoline-5-carbonitrile (30 mg, 0.190 mmol) in THF placed in a microwave vial were added sequentially 5-(tert-butyldimethylsilyloxy)-2-chloro-5,6,7,8-tetrahydroquinoline (67.8 mg, 0.228 mmol), K2CO3 (52.4 mg, 0.379 mmol), X-PHOS (7.23 mg, 0.015 mmol), and Pd2(dba)3 (3.47 mg, 3.79 μmol). The vial was sealed and flushed with argon. The mixture was heated in a microwave oven at 80° C. for 95 min. The mixture was cooled to RT and diluted with water and ethyl acetate. The organic layer was separated and the remaining aqueous layer was extracted with dichloromethane. The combined dichloromethane extracts were dried over sodium sulfate, filtered, and evaporated to dryness. Amount 32 mg. Yield 40%.

後処理

  1. customThe vial was sealed
  2. customflushed with argon
  3. temperatureThe mixture was cooled to RT
  4. additiondiluted with water and ethyl acetate
  5. customThe organic layer was separated
  6. extractionthe remaining aqueous layer was extracted with dichloromethane
  7. dry with materialThe combined dichloromethane extracts were dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness

出典と根拠

ORDレコード
ord-19337b4fe9dd42de91dfe4152946e219
出典データセット
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09266855B2

反応ノート

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