1-(5-amino-2,3-dihydro-1H-indol-1-yl)ethan-1-one → 1-Ethyl-5-aminoindoline

HRID 507354

반응식

HRID 507354 반응식
[C:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH2:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)(=O)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([NH2:13])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1)[CH3:2]

참가 물질

4

반응물 2

HCID 2925071-(5-amino-2,3-dihydro-1H-indol-1-yl)ethan-1-oneHCID 21226445Aluminium lithium hydride

생성물 1

HCID 230087101-Ethyl-5-aminoindoline수율 67%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 1-acetyl-5-aminoindoline (130 mg, 0.74 mmol) in anhydrous THF (10 mL) was added LiAlH4 (42 mg, 1.11 mmol). The mixture was stirred at rt for 6 h, quenched with saturated NH4Cl and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulphate and concentrated in vacuo to give a purple residue (80 mg, 67%) that was used without further purification. 1H NMR (270 MHz, DMSO): δ 6.56 (1H, s, ArH), 6.47 (1H, d broad, J=8.1 Hz, ArH), 6.37 (1H, d, J=8.0 Hz, ArH), 3.29 (2H, s, NH2), 3.20 (2H, t, J=7.6 Hz, CH2), 3.02 (2H, q, J=6.9 Hz, CH2), 2.86 (2H, t, J=7.6 Hz, CH2), 1.17 (3H, t, J=6.9 Hz, CH3).

후처리

  1. customquenched with saturated NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4d9553978bd54320a331925c76e285c2
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786152B2

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