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Chlorosuccinimide → 2-(9-Chloro-7-(3-cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

HRID 515735
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HRID 515735 반응식
[C:1]([C:3]1[CH:4]=[C:5]([CH:25]=[CH:26][C:27]=1[O:28][CH:29]([CH3:31])[CH3:30])[CH2:6][O:7][C:8]1[CH:16]=[CH:15][C:14]2[N:13]3[CH2:17][CH2:18][CH:19]([CH2:20][C:21]([OH:23])=[O:22])[C:12]3=[CH:11][C:10]=2[C:9]=1[CH3:24])#[N:2].[Cl:32]N1C(=O)CCC1=O>C(Cl)Cl>[Cl:32][C:11]1[C:10]2[C:9]([CH3:24])=[C:8]([O:7][CH2:6][C:5]3[CH:25]=[CH:26][C:27]([O:28][CH:29]([CH3:31])[CH3:30])=[C:3]([C:1]#[N:2])[CH:4]=3)[CH:16]=[CH:15][C:14]=2[N:13]2[CH2:17][CH2:18][CH:19]([CH2:20][C:21]([OH:23])=[O:22])[C:12]=12
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참가 물질

4

반응물 2

HCID 31398ChlorosuccinimideHCID 583295982-(7-(3-Cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid

생성물 1

HCID 583296012-(9-Chloro-7-(3-cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid수율 70.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a solution of 2-(7-(3-cyano-4-isopropoxybenzyloxy)-8-methyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl)acetic Acid (30 mg, 0.072 mmol) in DCM (2 mL) was added N-chlorosuccinimide (10.1 mg, 0.075 mmol) at 0° C. The reaction was stirred at that temperature for 40 min, diluted with DCM, washed with aqueous Na2S2O3 solution and water, and dried over anhydrous Na2SO4. The solvent was evaporated, and the residue was passed through a silica gel column with 5% MeOH/DCM to give the title compound as beige solid (23 mg). LCMS m/z=453.3 [M+H]+; 1H NMR (400 MHz, CDCl3) δ ppm 1.41 (d, J=6.0 Hz, 6H), 2.29-2.38 (m, 1H), 2.58 (dd, J=16.7, 10.5 Hz, 1H), 2.66 (s, 3H), 2.88-2.98 (m, 1H), 3.33 (dd, J=16.7, 3.7 Hz, 1H), 3.76-3.84 (m, 1H), 3.90-3.98 (m, 1H), 4.05-4.13 (m, 1H), 4.62-4.68 (m, 1H), 4.94 (s, 2H), 6.84 (d, J=8.8 Hz, 1H), 6.95-6.98 (m, 2H), 7.56-7.62 (m, 2H).

후처리

  1. washwashed with aqueous Na2S2O3 solution and water
  2. dry with materialdried over anhydrous Na2SO4
  3. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-46ef2418b4bc4b4388c6d45ac67ee575
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09108969B2

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