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Propanoyl bromide, 2-bromo- → 2-bromo-N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxoisoindolin-4-yl}propanamide

HRID 433295
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HRID 433295 반응식
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:29])[N:5]([CH:12]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH3:28])[CH:19]=1)[CH2:13][S:14]([CH3:17])(=[O:16])=[O:15])[C:6]2=[O:11].[Br:30][CH:31]([CH3:35])[C:32](Br)=[O:33].C(=O)(O)[O-].[Na+]>C(Cl)Cl.[Cl-].[Na+].O.CCOCC>[Br:30][CH:31]([CH3:35])[C:32]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:29])[N:5]([CH:12]([C:18]1[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[C:20]([O:26][CH2:27][CH3:28])[CH:19]=1)[CH2:13][S:14]([CH3:17])(=[O:15])=[O:16])[C:6]2=[O:11])=[O:33]
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참가 물질

7

반응물 3

HCID 79047Propanoyl bromide, 2-bromo-2회HCID 516892Sodium BicarbonateHCID 98449131H-Isoindole-1,3(2H)-dione, 4-amino-2-[(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-

생성물 1

HCID 187583882-bromo-N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxoisoindolin-4-yl}propanamide수율 76%

시약·촉매·용매 3

HCID 3283
Diethyl Ether
용매
HCID 6344Dichloromethane용매2회
HCID 57417360Sodium chloride; water용매

실험 절차

A solution of 4-amino-2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]isoindoline-1,3-dione (500 mg, 1.20 mmol) and 2-bromopropionyl bromide (0.140 mL, 1.34 mmol) in methylene chloride (10 mL) was stirred at room temperature overnight. An additional 0.1 mL of 2-bromopropionyl bromide (1 mol) was added and the mixture stirred overnight. To the mixture was added brine (4 mL), Sodium bicarbonate (sat, 10 mL) and methylene chloride (15 mL). The organic layer was separated, was washed with brine (10 mL), and dried over magnesium sulfate. The solvent was removed in vacuo to give a yellow oil. The oil was slurried in ether (10 mL). The resulting suspension was filtered and the solid washed with ether to give 2-bromo-N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxoisoindolin-4-yl}propanamide as a white solid (500 mg, 76% yield): 1H NMR (CDCl3) δ1.46 (t, J=6.9 Hz, 3H, CH3), 1.97 (d, J=6.9 Hz, 3H, CH3), 2.86 (s, 3H, CH3), 3.75 (dd, J=4.5, 14.4 Hz, 1H, CHH), 3.85 (s, 3H, CH3), 4.49-4.59 (m, 2H, CHH, CH), 4.09(q, J=6.9 Hz, 2H, CH2), 5.87 (dd, J=4.4, 10.3 Hz, 1H, NCH), 6.82-6.85 (m, 1H, Ar), 7.09-7.13 (m, 2H, Ar), 7.53 (d, J=7.3 Hz, 1H, Ar), 7.68 (t, J=7.5 Hz, 1H, Ar), 8.73 (d, J=8.4 Hz, 1H, Ar), 10.19 (s, 1H, NH); 13C NMR (CDCl3) δ14.61, 22.42, 41.54, 43.78, 48.67, 54.44, 55.87, 64.45, 111.39, 112.3, 116.10, 116.79, 120.35, 124.76, 129.14, 131.13, 136.02, 136.82, 148.55, 149.70, 167.28,168.42, 169.11.

후처리

  1. customThe organic layer was separated
  2. washwas washed with brine (10 mL)
  3. dry with materialdried over magnesium sulfate
  4. customThe solvent was removed in vacuo
  5. customto give a yellow oil
  6. filtrationThe resulting suspension was filtered
  7. washthe solid washed with ether

출처 및 근거

ORD 기록
ord-b470754169ca4df3a24513794b6045d5
출처 데이터셋
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06667316B1

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