Morpholine → 3,3,7-Trimethyl-6-morpholinoindolin-2-one

HRID 1618612ノート

反応式

HRID 1618612 の反応式
Br[C:2]1[C:10]([CH3:11])=[C:9]2[C:5]([C:6]([CH3:14])([CH3:13])[C:7](=[O:12])[NH:8]2)=[CH:4][CH:3]=1.CC([O-])(C)C.[Na+].[NH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.C(N1CCN2CCN(CC(C)C)P1N(CC(C)C)CC2)C(C)C>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:13][C:6]1([CH3:14])[C:5]2[C:9](=[C:10]([CH3:11])[C:2]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:3][CH:4]=2)[NH:8][C:7]1=[O:12]

参加物

7

反応物 4

HCID 8083MorpholineHCID 45712432,8,9-Triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo(3.3.3)undecaneHCID 23676156Sodium t-butoxideHCID 672855566-Bromo-3,3,7-trimethylindolin-2-one

生成物 1

HCID 672854763,3,7-Trimethyl-6-morpholinoindolin-2-one

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒

反応条件

温度
120 °C

実験手順

A mixture of 6-bromo-3,3,7-trimethylindolin-2-one (0.63 g, 2.44 mmol), NaOt-Bu (0.33 g, 3.42 mmol), Pd2(dba)3 (0.11 g, 0.12 mmol), morpholine (0.51 mL, 5.86 mmol), and 2,8,9-triisobutyl-2,5,8,9-tetraaza-1-phosphabicyclo[3.3.3]undecane (0.11 mL, 0.29 mmol) in Toluene (2.5 mL) was flushed with N2 for 10 minutes and then heated in a microwave at 120° C. for 80 minutes. The mixture was cooled to rt and concentrated. Purification of the residue by flash chromatography over silica gel, using 40% EtOAc in hexane, gave 3,3,7-trimethyl-6-morpholinoindolin-2-one. 1H-NMR (DMSO-d6) δ 10.27 (1H, s), 7.04 (1H, d, J=8.0 Hz), 6.64 (1H, d, J=8.0 Hz), 3.72 (4H, s), 2.78 (4H, s), 2.13 (3H, s), 1.21 (6H, s). Mass Spectrum (ESI) m/e=261.1 (M+1).

後処理

  1. customwas flushed with N2 for 10 minutes
  2. temperatureThe mixture was cooled to rt
  3. concentrationconcentrated
  4. customPurification of the residue by flash chromatography over silica gel

出典と根拠

ORDレコード
ord-d58ea449f1e14887a52268522dfd09cd
出典データセット
uspto-grants-2014_07
特許番号
US08765940B2

反応ノート

読み込み中…