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Toluene → 3-(4-Imidazol-1-ylmethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide

HRID 1644825
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HRID 1644825 반응식
[CH2:1]([C:5]1[S:9][C:8]([S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11])=[C:7](B(O)O)[CH:6]=1)[CH:2]([CH3:4])[CH3:3].Br[C:22]1[CH:33]=[CH:32][C:25]([CH2:26][N:27]2[CH:31]=[CH:30][N:29]=[CH:28]2)=[CH:24][CH:23]=1.C1(C)C=CC=CC=1.[OH-].[Na+]>CCOC(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[N:27]1([CH2:26][C:25]2[CH:24]=[CH:23][C:22]([C:7]3[CH:6]=[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[S:9][C:8]=3[S:10]([NH:13][C:14]([CH3:17])([CH3:16])[CH3:15])(=[O:12])=[O:11])=[CH:33][CH:32]=2)[CH:31]=[CH:30][N:29]=[CH:28]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 4

HCID 1140TolueneHCID 14798Sodium HydroxideHCID 29895571-(4-Bromobenzyl)-1H-imidazoleHCID 11484000(2-(N-(tert-Butyl)sulfamoyl)-5-isobutylthiophen-3-yl)boronic acid

생성물 1

HCID 114190423-(4-Imidazol-1-ylmethylphenyl)-5-iso-butyl-N-tert-butylthiophene-2-sulfonamide수율 63.4%

시약·촉매·용매 3

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 702Ethanol용매
HCID 8857Ethyl Acetate용매

실험 절차

5-iso-Butyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid (200.5 mg, 0.628 mmol, see step (c) above), 1-(4-bromobenzyl)-1H-imidazole (98.8 mg, 0.416 mmol, see step (d) above), toluene (15 mL), ethanol (15 mL), NaOH (1.0M, 1.5 mL, 1.5 mmol) and Pd(PPh3)4 (14.5 mg, 0.125 mmol) were mixed under N2. The mixture was warmed to reflux for 2 h. The mixture was diluted with EtOAc (50 mL), washed with water and brine, and dried over MgSO4. The solvent was removed and the residue was separated by column chromatography with chloroform:methanol (20:1) as an eluent to give 113.9 mg of the sub-title compound (yield: 63.27%).

후처리

  1. temperatureThe mixture was warmed
  2. temperatureto reflux for 2 h
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed
  6. customthe residue was separated by column chromatography with chloroform:methanol (20:1) as an eluent

출처 및 근거

ORD 기록
ord-835b1a2f8a6444638f8b3c0e987d67bd
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08124638B2

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