Sodium Carbonate → 3-{3-[2-(2-Ethylimidazol-1-yl)acetyl]phenyl}-5-iso-butyl-N-tert-butylthio-phene-2-sulfonamide

HRID 659699노트

반응식

HRID 659699 반응식
Br[C:2]1[CH:3]=[C:4]([C:8](=[O:17])[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[CH2:15][CH3:16])[CH:5]=[CH:6][CH:7]=1.[CH2:18]([C:22]1[S:26][C:25]([S:27]([NH:30][C:31]([CH3:34])([CH3:33])[CH3:32])(=[O:29])=[O:28])=[C:24](B(O)O)[CH:23]=1)[CH:19]([CH3:21])[CH3:20].C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)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>[CH2:15]([C:11]1[N:10]([CH2:9][C:8]([C:4]2[CH:3]=[C:2]([C:24]3[CH:23]=[C:22]([CH2:18][CH:19]([CH3:20])[CH3:21])[S:26][C:25]=3[S:27]([NH:30][C:31]([CH3:33])([CH3:32])[CH3:34])(=[O:29])=[O:28])[CH:7]=[CH:6][CH:5]=2)=[O:17])[CH:14]=[CH:13][N:12]=1)[CH3:16]

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 11484000(2-(N-(tert-Butyl)sulfamoyl)-5-isobutylthiophen-3-yl)boronic acidHCID 614053531-(3-Bromophenyl)-2-(2-ethylimidazol-1-yl)ethanone

생성물 1

HCID 671329483-{3-[2-(2-Ethylimidazol-1-yl)acetyl]phenyl}-5-iso-butyl-N-tert-butylthio-phene-2-sulfonamide수율 94%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매

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온도
80 °C

실험 절차

To a solution of 1-(3-bromophenyl)-2-(2-ethylimidazol-1-yl)ethanone (54.6 mg, 0.186 mmol; see step (a)) in toluene (10 mL) and ethanol (1 mL) was added 5-isobutyl-2-(N-tert-butylaminosulfonyl)thiophene-3-boronic acid (101 mg, 0.317 mmol; see Example 1(c)), Pd(PPh3)4 (12.9 mg, 0.0112 mmol), Na2CO3 (373 μL, 0.745 mmol, 2.0 M aq) and the reaction mixture was stirred for 4 h at 80° C. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc. The combined organic phase was dried (over anhydrous MgSO4), concentrated in vacuo, and the residue purified by flash chromatography using MeOH:CH2Cl2 (5:95) as eluent to give the sub-title compound as a colourless syrup in 94% yield (85.5 mg, 0.175 mmol).

후처리

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic phase was dried (over anhydrous MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe residue purified by flash chromatography

출처 및 근거

ORD 기록
ord-beec73cb9e194f069c0d3154decc27c4
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080571B2

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