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Sodium Iodide → 2-Butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid, 1-(acetyloxy)ethyl ester

HRID 1492491
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HRID 1492491 반응식
[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[CH:18][N:19]3[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]#[N:31])[C:7]([C:11]([OH:13])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[I-].[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O.[C:45]([O:48][CH2:49][CH3:50])(=[O:47])[CH3:46]>>[CH2:1]([C:5]1[N:6]([CH2:14][C:15]2[CH:23]=[CH:22][CH:21]=[C:20]3[C:16]=2[CH:17]=[CH:18][N:19]3[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[C:30]#[N:31])[C:7]([C:11]([O:13][CH:49]([O:48][C:45](=[O:47])[CH3:46])[CH3:50])=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 189503772-butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid

생성물 1

HCID 57250442
2-Butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid, 1-(acetyloxy)ethyl ester

실험 절차

2-Butyl-4-chloro-1-[[1-(2-cyanophenyl)-1H-indol-4-yl]methyl]-1H-imidazole-5-carboxylic acid (910 mg, 2.1 mmol, prepared as described in part C of Example 9), the title B compound (930 mg, 7.6 mmol), sodium iodide (795 mg, 5.03 mmol), cesium carbonate (2.6 g, 7.98 mmol) and dimethylformamide (4.0 mL) were combined and were stirred at room temperature for 16 hours. The reaction was diluted with ethyl acetate and filtered. The organic phase was washed with pH=4 buffer twice, pH 7 buffer once, saturated sodium chloride once, dried over anhydrous magnesium sulfate, filtered and concentrated to give a yellow oil. Purification by chromatography on Merck silica gel (250 g) eluting with (8:2) hexane/ethyl acetate gave the title B compound (1.06 g).

후처리

  1. filtrationfiltered
  2. washThe organic phase was washed with pH=4 buffer twice
  3. dry with materialpH 7 buffer once, saturated sodium chloride once, dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow oil
  7. customPurification by chromatography on Merck silica gel (250 g)
  8. washeluting with (8:2) hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-a345282878464c6a8a32c4d9636a29c7
출처 데이터셋
uspto-grants-1994_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05374615

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