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Sodium cyanoborohydride → Ethyl 5-(4-chlorobenzyl)-8-methoxy-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole-4-acetate

HRID 1034259
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HRID 1034259 반응식
[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[CH:13][C:12]([O:16][CH3:17])=[C:11]4[S:18][CH:19]([CH3:22])[C:20](=O)[C:9]([C:10]=34)=[C:8]2[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:4][CH:3]=1.[BH3-]C#N.[Na+]>ClCCCl.C(Cl)Cl.[Zn+2].[I-].[I-]>[Cl:1][C:2]1[CH:30]=[CH:29][C:5]([CH2:6][N:7]2[C:15]3[CH:14]=[CH:13][C:12]([O:16][CH3:17])=[C:11]4[S:18][CH:19]([CH3:22])[CH2:20][C:9]([C:10]=34)=[C:8]2[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:4][CH:3]=1
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참가 물질

6

반응물 2

HCID 5003444Sodium cyanoborohydrideHCID 19023688Ethyl 5-(4-chlorobenzyl)-8-methoxy-2-methyl-3,5-dihydro-3-oxo-2H-thiopyrano[4,3,2-cd]indole-4-acetate

생성물 1

HCID 19023676Ethyl 5-(4-chlorobenzyl)-8-methoxy-2-methyl-3,5-dihydro-2H-thiopyrano[4,3,2-cd]indole-4-acetate

시약·촉매·용매 3

HCID 9883512zinc(II)iodide촉매HCID 111,2-Dichloroethane
용매
HCID 6344Dichloromethane용매

실험 절차

To a suspension of product from Step 2 (886 mg) in 1,2-dichloroethane (16 mL) there was added ZnI2 (960 mg) and NaCNBH3 (440 mg). The mixture was heated to 60° for 1 hour, cooled, diluted with CH2Cl2, washed 3× with H2O, dried over Na2SO4, filtered and evaporated to afford the title product as an oil which slowly solidified. It was used as such in the next step.

후처리

  1. temperatureThe mixture was heated to 60° for 1 hour
  2. temperaturecooled
  3. washwashed 3× with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated

출처 및 근거

ORD 기록
ord-9412861b86ad4714af60a2f5c3b21bf8
출처 데이터셋
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05314898

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