Oxindole → HCID 69662062, 화합물

HRID 1829058노트

반응식

HRID 1829058 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH3:21][N:22]([CH2:24][CH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](=O)[O:26]1)[CH3:23].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1COCC1>C(COC)OC.C1COCC1>[CH3:23][N:22]([CH2:24][CH:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:27](=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])[O:26]1)[CH3:21]

참가 물질

7

반응물 4

HCID 321710OxindoleHCID 2733832Lithium HexamethyldisilazideHCID 220615043-[(Dimethylamino)methyl]-2-benzofuran-1(3H)-oneHCID 23714775LiHMDS tetrahydrofuran

생성물 1

HCID 69662062HCID 69662062, 화합물수율 24.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 80711,2-Dimethoxyethane용매2회

실험 절차

To a solution of oxindole (205 mg, 1.54 mmol) in dimethoxyethane (4.0 ml) at room temperature was added 1.0M LiHMDS in THF (1.54 ml). After stirring for 10 minutes at room temperature, 3-dimethylaminomethyl-3H-isobenzofuran-1-one (235 mg, 1.23 mmol) in dimethoxyethane (0.5 ml) was added and the mixture was stirred rapidly for 1 hour. Additional 1.0M LiHMDS/THF (1.54 ml) was added. After 2 hours the reaction was quenched into 10% HCl (50 ml) and 25 ml water added. The aqueous layer was washed with EtOAc and then basified with saturated NaHCO3 aqueous solution. The aqueous layer was extracted with EtOAc. The EtOAc layer was washed with brine, dried over anhydrous Na2SO4, and rotary evaporated to provide a yellow solid. The yellow solid was chromatographed silica gel column (CHCl3 to 2.5% MeOH/CHCl3 gradient) and then recrystallized from MeOH to give 3-(3-dimethylaminomethy-3H-isobenzofuran-1-ylidene)-1,3-dihydro-indol-2-one as yellow needles (92 mg, 24%).

후처리

  1. stirringthe mixture was stirred rapidly for 1 hour
  2. customAfter 2 hours the reaction was quenched into 10% HCl (50 ml) and 25 ml water
  3. additionadded
  4. washThe aqueous layer was washed with EtOAc
  5. extractionThe aqueous layer was extracted with EtOAc
  6. washThe EtOAc layer was washed with brine
  7. dry with materialdried over anhydrous Na2SO4
  8. customrotary evaporated
  9. customto provide a yellow solid
  10. customThe yellow solid was chromatographed silica gel column (CHCl3 to 2.5% MeOH/CHCl3 gradient)
  11. customrecrystallized from MeOH

출처 및 근거

ORD 기록
ord-b5f848af52d845f6b7f939f1b275e9ee
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07060844B2

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